Substituted phenyl keto enols as pesticides and herbicides

ABSTRACT

The present invention relates to novel compounds of the formula (I)  
                 
 
     in which  
     Het represents one of the groups  
                 
 
     in which  
     A, B, D, G, V, W, X, Y and Z are as defined in the description, processes and intermediates for their preparation, and to their use as pesticides and herbicides.

[0001] The invention relates to novel phenyl-substituted cyclicketoenols, a plurality of processes and intermediates for theirpreparation and their use as pesticides and herbicides.

[0002] It has already been disclosed that certain phenyl-substitutedcyclic ketoenols are active as insecticides, acaricides and/orherbicides.

[0003] Pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones havepreviously been described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120(1967)). Furthermore, N-phenylpyrrolidine-2,4-diones have beensynthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem.1985, 1095). Biological activity has not been disclosed for thesecompounds.

[0004] EP-A-0 262 399 and GB-A-2 266 888 disclose compounds(3-aryl-pyrrolidine-2,4-diones) of a similar structure, for which,however, no herbicidal, insecticidal or acaricidal activity has beendisclosed. Unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dionederivatives (EP-A-355 599 and EP-A-415 211) and substituted monocyclic3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077)with herbicidal, insecticidal or acaricidal activity are known.

[0005] Polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073)and 1H-aryl-pyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334,EP-A-596 298, EP-A-613 884, EP-A-613 885, DE 44 40 594, WO 94/01 997, WO95/01 358, WO 95/20 572, EP-A-668 267 and WO 95/26 954) are also known.

[0006] It is known that certain substituted Δ³-dihydrofuran-2-onederivatives have herbicidal properties (cf. DE-A-4 014 420). Thesynthesis of the tetronic acid derivatives used as starting materials(such as, for example,3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-Δ³-dihydrofuran-2-one)is likewise described in DE-A-4 014 420. Compounds of similar structurewithout details of an insecticidal and/or acaricidal activity are knownfrom the publication Campbell et al., J. Chem. Soc., Perkin Trans. 1,1985, (8) 1567-76. Furthermore, 3-aryl-Δ³-dihydrofuranone derivativeshaving herbicidal, acaricidal and insecticidal properties are disclosedin EP-A-528 156 and EP-A-0 647 637. 3-Aryl-Δ³-dihydrothiophen-onederivatives are known (WO 95/26 345).

[0007] Certain phenyl-pyrone derivatives unsubstituted in the phenylring have already been disclosed (cf. A. M. Chirazi, T. Kappe and E.Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K.Heidenbluth, Chem. Ber 91, 2849), a possible utility for these compoundsas pesticides not being indicated. Phenyl-pyrone derivatives substitutedin the phenyl ring and having herbicidal, acaricidal and insecticidalproperties are described in EP-A-588 137.

[0008] Certain 5-phenyl-1,3-thiazine derivatives unsubstituted in thephenyl ring have already been described (cf. E. Ziegler and E. Steiner,Monatsh. 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J.Heterocycl. Chem. 10, 223 (1973)), a possible utility as pesticides notbeing indicated for these compounds. 5-Phenyl-1,3-thiazine derivativessubstituted in the phenyl ring and having herbicidal, acaricidal andinsecticidal activity are described in WO 94/14 785.

[0009] However, the acaricidal and insecticidal activity and/or spectrumof action, and/or the toleration of these compounds by plants, inparticular by crops, is not always satisfactory.

[0010] There have now been found a novel compounds of the formula (I)

[0011] in which

[0012] V represents hydrogen, halogen, alkyl or alkoxy,

[0013] W represents cyano, nitro, halogen, alkyl, alkenyl, alkinyl,alkoxy, halogenoalkyl, halogenoalkoxy, respectively optionallysubstituted phenyl, phenoxy, phenylthio, phenylalkoxy orphenylalkylthio,

[0014] X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy,halogenoalkyl, halogenoalkoxy, cyano, nitro or respectively optionallysubstituted phenyl, phenoxy, phenylthio, phenylalkyloxy orphenylalkylthio,

[0015] Y represents hydrogen, halogen, alkyl alkoxy, halogenoalkyl,halogenoalkoxy, cyano or nitro,

[0016] Z represents halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionallysubstituted phenoxy, phenylthio, 5- to 6-membered hetaryloxy, 5- to6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or

[0017] Y and Z represent together with the carbon atoms that they areattached to an optionally substituted cycle which is optionallyinterrupted by one or more hetero atoms, V, X and W having one of theabovementioned meanings, or

[0018] W and Z represent together with the carbon atoms that they areattached to an optionally substituted cycle which is optionallyinterrupted by one or more heteroatoms, V, X and Y having one of theabovementioned meanings,

[0019] Het represents one of the groups

[0020]  in which

[0021] A represents hydrogen, respectively optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl oralkylthioalkyl, respectively saturated or unsaturated and optionallysubstituted cycloalkyl or heterocyclyl or respectively optionallyhalogen-, alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- ornitro- substituted aryl, arylalkyl or hetaryl,

[0022] B represents hydrogen, alkyl or alkoxyalkyl, or

[0023] A and B represent together with the carbon atom that they areattached to a saturated or unsaturated optionally substituted carbocycleor heterocycle,

[0024] D represents hydrogen or an optionally substituted radical fromthe group consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl,polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl,saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl orhetaryl, or

[0025] A and D represent together with the atoms that they are attachedto a respectively optionally substituted carbocycle or heterocycle,

[0026] G represents hydrogen (a) or one of the groups

[0027]  in which,

[0028] E represents a metal ion equivalent or an ammonium ion,

[0029] L represents oxygen or sulphur,

[0030] M represents oxygen or sulphur,

[0031] R¹ represents respectively optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or respectivelyoptionally halogen-, alkyl- or alkoxy- substituted cycloalkyl orheterocyclyl or respectively optionally substituted phenyl, phenylalkyl,hetaryl, phenoxyalkyl or hetaryloxyalkyl,

[0032] R² represents respectively optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl or polyalkoxyalkyl or respectively optionallysubstituted cycloalkyl, phenyl or benzyl,

[0033] R³, R⁴ and R⁵ each represent independently of one anotherrespectively optionally halogen-substituted alkyl, alkoxy, alkylamino,dialkylamino, alkylthio, alkenylthio or cycloalkylthio or respectivelyoptionally substituted phenyl, benzyl, phenoxy or phenylthio,

[0034] R⁶ and R⁷ each represent independently of one another hydrogen,respectively optionally halogen-substituted alkyl, cycloalkyl, alkenyl,alkoxy or alkoxyalkyl or respectively optionally substituted phenyl orbenzyl, or represent together with the N-atom that they are attached toan optionally oxygen- or sulphur- containing and optionally substitutedcycle,

[0035] excluding the following compounds

[0036] The compounds of the formula (I) can also be present, dependingon the nature of the substituents, as geometric and/or optical isomersor isomer mixtures of differing composition which, if appropriate, canbe separated in a customary manner. Both the pure isomers and the isomermixtures, their preparation and use, and compositions containing themare part of the subject matter of the present invention. In thefollowing, for simplicity, however, compounds of the formula (I) arealways referred to, although both pure compounds and, if appropriate,mixtures having different proportions of isomer compounds are intended.

[0037] Including the meanings (1) to (5) of the group Het, the followingprincipal structures (I-1) to (I-5) result:

[0038] in which

[0039] A, B, D, G, V, W, X, Y and Z are each as defined above.

[0040] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-1-a) to(I-1-g) result if Het represents the group (1)

[0041] in which

[0042] A, B, E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areeach as defined above

[0043] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-2-a) to(I-2-g) result if Het represents the group (2)

[0044] in which

[0045] A, B, E, L, M, V, W, X, Y Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areeach as defined above.

[0046] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-3-a) to(I-3-g) result if Het represents the group (3)

[0047] in which

[0048] A, B, E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areeach as defined above.

[0049] Depending on the position of the substituent G, the compounds ofthe formula (I-4) can be present in the two isomeric forms of formulae(I-4)_(a) and (I-4)_(b)

[0050] which is intended to be expressed by the dashed line in theformula (I-4).

[0051] The compounds of the formulae (I-4)_(a) and (I-4)_(b) can bepresent both as mixtures and in the form of their pure isomers. Mixturesof the compounds of the formulae (I-4)_(a) and (I-4)_(b) can, ifdesired, be separated by physical methods in a manner known per se, forexample by chromatographic methods.

[0052] For better clarity, in the following in each case only one of thepossible isomers is shown. This does not exclude the possibility thatthe compounds can optionally be present in the form of the isomermixtures or in the other respective isomer form

[0053] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-4-a) to(I-4-g) result if Het represents the group (4)

[0054] in which

[0055] A, D, E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ areeach as defined above.

[0056] Including the various meanings (a), (b), (c), (d), (e), (f) and(g) of the group G, the following principal structures (I-5-a) to(I-5-g) result if Het represents the group (5)

[0057] in which

[0058] A, E, L, M, V, W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are eachas defined above.

[0059] Furthermore, it has been found that the novel compounds of theformula (I) are obtained by one of the processes described below:

[0060] (A) Compounds of the formula (I-1-a)

[0061]  in which

[0062] A, B, V, W, X, Y and Z are each as defined above, are obtained bythe intramolecular condensation of compounds of the formula (II)

[0063]  in which,

[0064] A, B, V, W, X, Y and Z are each as defined above and

[0065] R⁸ represents alkyl (preferably C₁-C₆-alkyl)

[0066] in the presence of a diluent and in the presence of a base.

[0067] (B) Furthermore, it was found that compounds of the formula(I-2-a)

[0068]  in which

[0069] A, B, V, W, X, Y and Z are each as defined above are obtained bythe intramolecular condensation of compounds of the formula (III)

[0070]  in which

[0071] A, B, V, W, X, Y, Z and R⁸ are each as defined above

[0072] in the presence of a diluent and in the presence of a base.

[0073] (C) Furthermore, it was found that compounds of the formula(I-3-a)

[0074]  in which

[0075] A, B, V, W, X, Y and Z are each as defined above are obtained bythe intramolecular cyclization of compounds of formula (IV)

[0076]  in which

[0077] A, B, V, W, X, Y, Z and R⁸ are each as defined above and

[0078] T represents hydrogen, halogen, alkyl (preferably C₁-C₆-alkyl) oralkoxy (preferably C₁-C₈-alkoxy),

[0079] if appropriate in the presence of a diluent and in the presenceof an acid.

[0080] (D) Furthermore, it was found that compounds of the formula(I-4-a)

[0081]  in which

[0082] A, D, V, W, X, Y and Z are each as defined above are obtained byreacting compounds of the formula (V)

[0083]  in which

[0084] A and D are each as defined above

[0085] or their silyl enol ethers of the formula (Va)

[0086]  in which

[0087] A and D are each as defined above and

[0088] R^(8′) represents alkyl (preferably methyl)

[0089] with compounds of the formula (VI)

[0090]  in which

[0091] V, W, X, Y and Z are each as defined above and

[0092] Hal represents halogen (preferably chlorine or bromine),

[0093] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid acceptor.

[0094] (E) Furthermore, it was found that compounds of the formula(I-5-a)

[0095]  in which

[0096] A, V, W, X, Y and Z are each as defined above

[0097] are obtained by reacting compounds of the formula (VII)

[0098]  in which

[0099] A is as defined above

[0100] with compounds of the formula (VI)

[0101]  in which

[0102] Hal, V, W, X, Y and Z are each as defined above,

[0103] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid acceptor.

[0104] In addition, it has been found

[0105] (F) that the compounds of the formulae (I-1-b) to (I-5-b) shownabove in which A, B, D, R¹, V, W, X, Y and Z are each as defined aboveare obtained by reacting compounds of the formulae (I-1-a) to (I-5-a)shown above in which A, B, D, V, W, X, Y and Z are each as defined above

[0106] α) with acid halides of the formula (VIII)

[0107]  in which

[0108] R¹ is as defined above and

[0109] Hal represents halogen (in particular chlorine or bromine) or

[0110] β) with carboxylic anhydrides of the formula (IX)

R¹—CO—O—CO—R¹   (IX)

[0111]  in which

[0112] R¹ is as defined above,

[0113] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid-binding agent;

[0114] (G) that the compounds of the formulae (I-1-c) to (I-5-c) shownabove in which A, B, D, R², V, W, M, X, Y and Z are each as definedabove and L represents oxygen are obtained by reacting compounds of theformulae (I-1-a) to (I-5-a) shown above in which A, B, D, V, W, X, Y andZ are each as defined above in each case

[0115] with chloroformic esters or chloroformic thioesters of theformula (X)

R²—M—CO—Cl   (X)

[0116]  in which

[0117] R² and M are each as defined above,

[0118] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid-binding agent;

[0119] (H) that compounds of the formulae (I-1-c) to (I-5-c) shown abovein which A, B, D, R², V, W, M, X, Y and Z are each as defined above andL represents sulphur are obtained by reacting compounds of the formulae(I-1-a) to (I-5-a) shown above in which A, B, D, V, W, X, Y and Z areeach as defined above in each case

[0120] α) with chloromonothioformic esters or chlorodithioformic estersof the formula (XI)

[0121]  in which

[0122] M and R² are each as defined above,

[0123] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid-binding agent or

[0124] β) with carbon disulphide and subsequently with compounds of theformula (XII)

R²-Hal   (XII)

[0125]  in which

[0126] R² is as defined above and

[0127] Hal represents chlorine, bromine or iodine,

[0128] if appropriate in the presence of a diluent and if appropriate inthe presence of a base,

[0129] (I) that compounds of the formulae (I-1-d) to (I-5-d) shown abovein which A, B, D, R³, V, W, X, Y and Z are each as defined above areobtained by reacting compounds of the formulae (I-1-a) to (I-5-a) shownabove in which A, B, D, V, W, X, Y and Z are each as defined above ineach case

[0130] with sulphonyl chlorides of the formula (XIII)

R³—SO₂—Cl   (XII)

[0131]  in which

[0132] R³ is as defined above,

[0133] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid-binding agent,

[0134] (J) that compounds of the formulae (I-1-e) to (I-5-e) shown abovein which A, B, D, L, R⁴, R⁵, V, W, X, Y and Z are each as defined aboveare obtained by reacting compounds of the formulae (I-1-a) to (I-4-a)shown above in which A, B, D, V, W, X, Y and Z are each as defined abovein each case

[0135] with phosphorus compounds of the formula (XIV)

[0136]  in which

[0137] L, R⁴ and R⁵ are each as defined above and

[0138] Hal represents halogen (in particular chlorine or bromine),

[0139] if appropriate in the presence of a diluent and if appropriate inthe presence of acid-binding agent,

[0140] (K) that compounds of the formulae (I-1-f) to (I-5-f) shown abovein which A, B, D, E, V, W, X, Y and Z are each as defined above areobtained by reacting compounds of the formulae (I-1-a) to (I-5-a) inwhich A, B, D, V, W, X, Y and Z are each as defined above in each case

[0141] with metal compounds or amines of the formulae (XV) or (XVI)

[0142]  in which

[0143] Me represents a mono- or divalent metal (preferably an alkalimetal or an alkaline earth metal such as lithium, sodium, potassium,magnesium or calcium),

[0144] t represents the number 1 or 2 and

[0145] R¹⁰, R¹¹, R¹² each represent independently of one anotherhydrogen or alkyl (preferably C₁-C₈-alkyl),

[0146] if appropriate in the presence of a diluent,

[0147] (L) that compounds of the formulae (I-1-g) to (I-5-g) shownabove, in which A, B, D, L, R⁶, R⁷, V, W, X, Y and Z are each as definedabove, are obtained by reacting compounds of the formulae (I-1-a) to(I-5-a) shown above, in which A, B, D, V, W, X, Y and Z are each asdefined above, in each case

[0148] α) with isocyanates or isothiocyanates of the formula (XVII)

R⁶—N═C═L   (XVII)

[0149]  in which

[0150] R⁶ and L are each as defined above,

[0151] if appropriate in the presence of a diluent and if appropriate inthe presence of a catalyst or

[0152] β) with carbamoyl chlorides or thiocarbamoyl chlorides of theformula (XVIII)

[0153]  in which

[0154] L, R⁶ and R⁷ are each as defined above,

[0155] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid-binding agent.

[0156] Furthermore, it has surprisingly been found that the novelcompounds of the formula (I) have very good activity as pesticides,preferably as insecticides, acaricides and, as herbicides, and that theyadditionally are very well tolerated by plants, in particular by crops.

[0157] Formula (I) provides a general definition of the compoundsaccording to the invention Preferred substituents or ranges of theradicals shown in the formulae mentioned hereinabove and hereinbelow areillustrated below

[0158] V preferably represents hydrogen, halogen, C₁-C₆-alkyl orC₁-C₆-alkoxy.

[0159] W preferably represents cyano, nitro, halogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy or respectively optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl, phenoxy, phenylthio, phenyl-C₁-C₄-alkoxy orphenyl-C₁-C₄-alkylthio,

[0160] X preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, cyano, nitro or respectively optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,phenylthio, phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio,

[0161] Y preferably represents hydrogen, halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, cyano or nitro,

[0162] Z preferably represents halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, hydroxyl, cyano, nitro orrespectively optionally halogen-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenoxy, phenylthio, thiazolyloxy, pyridinyloxy, pyrimidyloxy,pyrazolyloxy, phenyl-C₁-C₄-alkyloxy or phenyl-C₁-C-alkylthio, or,

[0163] Y and Z together preferably represent respectively optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₅-alkanediyl or C₃-C₅-alkenediyl in which one to three members canbe optionally replaced independently of one another by oxygen, sulphur,nitrogen or a carbonyl group, or

[0164] W and Z together preferably represent respectively optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substitutedC₃-C₅-alkanediyl or C₃-C₅-alkenediyl in which one to three members canbe optionally replaced independently of one another by oxygen, sulphur,nitrogen or a carbonyl group.

[0165] Het preferably represents one of the groups

[0166] A preferably represents hydrogen, respectively optionallyhalogen-substituted C₁-C₁₂-alkyl, C₂-C₈-alkenyl,C₁-C₁₀-alkoxy-C₁-C₈-alkyl, poly-C₁-C₈-alkoxy-C₁-C₈-alkyl orC₁-C₁₀-alkylthio-C₁-C₆-alkyl, optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one or twonot directly adjacent methylene groups are replaced by oxygen and/orsulphur, or preferably represents respectively optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl, naphthyl,phenyl-C₁-C₆-alkyl, naphthyl-C₁-C₆-alkyl or hetaryl having 5 or 6 ringatoms and one to three heteroatoms from the group consisting of oxygen,sulphur and nitrogen.

[0167] B preferably represents hydrogen, C₁-C₁₂-alkyl orC₁-C₈-alkoxy-C₁-C₆-alkyl or

[0168] A, B and the carbon atom that they are attached to preferablyrepresent C₃-C₁₀-cycloalkyl or C₅-C₁₀-cycloalkenyl where in each caseone methylene group is optionally replaced by oxygen or sulphur andwhich are optionally substituted by C₁-C₈-alkyl, C₃-C₁₀-cycloalkyl,C₁-C₈-halogenoalkyl, C₁-C₈-alkoxy, C₁-C₈-alkylthio, halogen or phenyl,or

[0169] A, B and the carbon atom that they are attached to preferablyrepresent C₅-C₆-cycloalkyl which is substituted by an alkylenediyl groupoptionally containing one or two oxygen and/or sulphur atoms, or by analkylenedioxy group or alkylenedithioyl group forming a further five- toeight-membered ring with the carbon atom that it is attached to, or

[0170] A, B and the carbon atom that they are attached to preferablyrepresent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in which two carbonatoms are connected by respectively optionally C₁-C₆-alkyl-,C₁-C₆-alkoxy- or halogen-substituted C₃-C₆-alkanediyl, C₃-C₆-alkenediylor C₄-C₆-alkanedienediyl where in each case one methylene group isoptionally replaced by oxygen or sulphur.

[0171] D preferably represents hydrogen, respectively optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkinyl,C₁-C₁₀-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl orC₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₈-cycloalkyl inwhich optionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur, or preferably represents respectivelyoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl, hetarylhaving 5 to 6 ring atoms and one or two heteroatoms from the groupconsisting of oxygen, sulphur and nitrogen, phenyl-C₁-C₆-alkyl orhetaryl-C₁-C₆-alkyl having 5 to 6 ring atoms and one or two heteroatomsfrom the group consisting of oxygen, sulphur and nitrogen, or

[0172] A and D together preferably represent a C₃-C₆-alkanediyl,C₃-C₆-alkenediyl or C₄-C₆-alkadienediyl group in which in each case onemethylene group is optionally replaced by oxygen or sulphur and whichare respectively optionally substituted by halogen or by respectivelyoptionally halogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₃-C₇-cycloalkyl, phenyl or benzyloxy or by a furtherC₃-C₆-alkanediyl, C₃-C₆-alkenediyl or C₄-C₆-alkadienediyl group forminga fused-on ring where in each case one methylene group is optionallyreplaced by oxygen or sulphur and which are optionally substituted byC₁-C₆-alkyl, or

[0173] A and D together represent a C₃-C₆-alkanediyl or C₃-C₆-alkenediylgroup, each of which optionally contains one of the following groups

[0174] G preferably represents hydrogen (a) or one of the groups

[0175]  in which

[0176] E represents a metal ion equivalent or an ammonium ion,

[0177] L represents oxygen or sulphur and

[0178] M represents oxygen or sulphur.

[0179] R¹ preferably represents respectively optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl or respectively halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which one or two notdirectly adjacent methylene groups are optionally replaced by oxygenand/or sulphur,

[0180] optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-, C₁-C₆-alkylthio- orC₁-C₆-alkylsulphonyl-substituted phenyl,

[0181] optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl,

[0182] optionally halogen- or C₁-C₆-alkyl-substituted 5- or 6-memberedhetaryl having one or two heteroatoms from the group consisting ofoxygen, sulphur and nitrogen,

[0183] optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl or

[0184] optionally halogen-, amino- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryloxy-C₁-C₆-alkyl having one or two heteroatoms from thegroup consisting of oxygen, sulphur and nitrogen.

[0185] R² preferably represents respectively optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl or poly-C₁-C₈-alkoxy-C₂-C₈-alkyl,

[0186] optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl or

[0187] respectively optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl or C₁-C₆-halogenoalkoxy-substitutedphenyl or benzyl.

[0188] R³ preferably represents optionally halogen-substitutedC₁-C₈-alkyl or respectively optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano- ornitro-substituted phenyl or benzyl.

[0189] R⁴ and R⁵ each preferably represent independently of one anotherrespectively optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio orC₃-C₈-alkenylthio, respectively optionally halogen-, nitro-, cyano-,C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-halogenoalkylthio-, C₁-C₄-alkyl- orC₁-C₄-halogenoalkyl-substituted phenyl, phenoxy or phenylthio.

[0190] R⁶ and R⁷ preferably represent independently of one anotherhydrogen, respectively optionally halogen-substituted C₁-C₈-alkyl,C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl orC₁-C₈-alkoxy-C₂-C₈-alkyl, respectively optionally halogen-,C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- or C₁-C₈-alkoxy-substituted phenyl orbenzyl or together represent an optionally C₁-C₆-alkyl-substitutedC₃-C₆-alkylene radical in which one methylene group is optionallyreplaced by oxygen or sulphur.

[0191] R¹³ preferably represents hydrogen or respectively optionallyhalogen-substituted C₁-C₈-alkyl or C₁-C₈-alkoxy, optionally halogen-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which onemethylene group is optionally replaced by oxygen or sulphur, orrespectively optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy.

[0192] R¹⁴ preferably represents hydrogen or C₁-C₈-alkyl or

[0193] R¹³ and R¹⁴ together preferably represent C₄-C₆-alkanediyl.

[0194] R¹⁵ and R¹⁶ are identical or different and preferably representC₁-C₆-alkyl or

[0195] R¹⁵ and R¹⁶ together preferably represent a C₂-C₄-alkanediylradical which is optionally substituted by C₁-C₆-alkyl or by optionallyhalogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl.

[0196] R¹⁷ and R¹⁸ each preferably represent independently of oneanother hydrogen, optionally halogen-substituted C₁-C₈-alkyl oroptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl or

[0197] R¹⁷ and R¹⁸ preferably represent together with the carbon atomthat they are attached to optionally C₁-C₄-alkyl-substitutedC₅-C₇-cycloalkyl in which one methylene group is optionally replaced byoxygen or sulphur.

[0198] R¹⁹ and R²⁰ each preferably represent independently of oneanother C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino,C₃-C₁₀-alkenylamino, di-(C ₁-C₁₀-alkyl)amino ordi-(C₃-C₁₀-alkenyl)amino).

[0199] V particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl or C₁-C₄-alkoxy.

[0200] W particularly preferably represents cyano, nitro, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy or respectively optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,benzyl or benzyloxy.

[0201] X particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano, nitro or respectively optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,benzyl or benzyloxy.

[0202] Y particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro.

[0203] Z particularly preferably represents fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy,hydroxyl, cyano, nitro or respectively optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenoxy or benzyloxy,or

[0204] Y and Z together particularly preferably represent respectivelyoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-or C₁-C₂-halogenoalkyl-substituted C₃-C₄-alkanediyl or C₃-C₄-alkenediylin which optionally one or two not directly adjacent members arereplaced independently of one another by oxygen, sulphur or nitrogen, or

[0205] W and Z together particularly preferably represent respectivelyoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-or C₁-C₂-halogenoalkyl-substituted C₃-C₄-alkanediyl or C₃-C₄-alkenyldiylin which optionally one or two not directly adjacent members arereplaced independently of one another by oxygen, sulphur or nitrogen.

[0206] Het particularly preferably represents one of the groups

[0207] A particularly preferably represents hydrogen, respectivelyoptionally fluorine- or chlorine-substituted C₁-C₁₀-alkyl,C₂-C₆-alkenyl, C₁-C₈-alkoxy-C₁-C₆-alkyl, poly-C₁-C₆-alkoxy-C₁-C₆-alkylor C₁-C₈-alkylthio-C₁-C₆-alkyl or optionally fluorine-, chlorine-,C₁-C₄-alkyl- or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl in which oneor two not directly adjacent methylene groups are optionally replaced byoxygen and/or sulphur, or respectively optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl, furanyl,pyridyl, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienylor phenyl-C ₁-C₄-alkyl.

[0208] B particularly preferably represents hydrogen, C₁-C₁₀-alkyl orC₁-C₆-alkoxy-C₁-C₄-alkyl or

[0209] A, B and the carbon atom that they are attached to particularlypreferably represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in whichrespectively optionally one methylene group is replaced by oxygen orsulphur and which are optionally substituted by C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₁-C₃-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,fluorine, chlorine or phenyl, or

[0210] A, B and the carbon atom that they are attached to particularlypreferably represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl group optionally containing one or two oxygen or sulphuratoms, or by an alkylenedioxy or alkylenedithiol group forming a furtherfive- to seven-membered ring with the carbon atom that it is attached toor

[0211] A, B and the carbon atom that they are attached to particularlypreferably represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which twocarbon atoms are connected by respectively optionally C₁-C₄-alkyl-,C₁-C₄-alkoxy-, fluorine-, chlorine- or bromine-substitutedC₃-C₅-alkanediyl, C₃-C₅-alkenediyl or butadienediyl in whichrespectively optionally one methylene group is replaced by oxygen orsulphur.

[0212] D particularly preferably represents hydrogen, respectivelyoptionally fluorine- or chlorine-substituted C₁-C₁₀-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₁-C₈-alkoxy-C₂-C₆-alkyl,poly-C₁-C₆-alkoxy-C₂-C₆-alkyl or C₁-C₈-alkylthio-C₂-C₆-alkyl, optionallyfluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which one or two notdirectly adjacent methylene groups are optionally replaced by oxygenand/or sulphur, or particularly preferably represents respectivelyoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, cyano- ornitro-substituted phenyl, furanyl, imidazolyl, pyridyl, thiazolyl,pyrazolyl, pyrimidyl, pyrrolyl, thienyl, triazolyl or phenyl-C₁-C₄-alkylor

[0213] A and D together particularly preferably represent aC₃-C₅-alkanediyl or C₃-C₅-alkenediyl group in which respectivelyoptionally one carbon atom is replaced by oxygen or sulphur and whichare optionally substituted by fluorine, chlorine or respectivelyoptionally fluorine- or chlorine-substituted C₁-C₆-alkyl, C₁-C₄-alkoxy,C₁-C₄-alkylthio, C₃-C₆-cycloalkyl, phenyl or benzyloxy or whichrespectively optionally contain one of the following groups:

[0214] G particularly preferably represents hydrogen (a) or one of thegroups

[0215]  in which

[0216] E represents a metal ion equivalent or an ammonium ion,

[0217] L represents oxygen or sulphur and

[0218] M represents oxygen or sulphur.

[0219] R¹ particularly preferably represents respectively optionallyfluorine- or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl orpoly-C₁-C₆-alkoxy-C₁-C₆-alkyl or optionally fluorine-, chlorine-,C₁-C₅-alkyl- or C₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in which oneor two not directly adjacent methylene groups are optionally replaced byoxygen and/or sulphur,

[0220] optionally fluorine-, chlorine-, bromine-, cyano-, nitro-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl,

[0221] optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substitutedphenyl-C₁-C₄-alkyl,

[0222] optionally fluorine-, chlorine-, bromine- orC₁-C₄-alkyl-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl,furanyl or thienyl,

[0223] optionally fluorine-, chlorine-, bromine- orC₁-C₄-alkyl-substituted phenoxy-C ₁-C₅-alkyl or

[0224] respectively optionally fluorine-, chlorine-, bromine-, amino- orC₁-C₄-alkyl-substituted pyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkylor thiazolyloxy-C ₁-C₅-alkyl.

[0225] R² particularly preferably represents respectively optionallyfluorine- or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl,

[0226] optionally fluorine-, chlorine-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl or

[0227] respectively optionally fluorine-, chlorine-, bromine-, cyano-,nitro-, C₁-C₄-alkyl-, C₁-C₃-alkoxy-, C₁-C₃-halogenoalkyl- orC₁-C₃-halogenoalkoxy-substituted phenyl or benzyl.

[0228] R³ particularly preferably represents optionally fluorine- orchlorine-substituted C₁-C₆-alkyl or respectively optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkoxy-,C₁-C₂-halogenoalkyl-, cyano- or nitro-substituted phenyl or benzyl.

[0229] R⁴ and R⁵ each particularly preferably represent independently ofone another respectively optionally fluorine- or chlorine-substitutedC₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino,C₁-C₆-alkylthio or C₃-C₄-alkenylthio or respectively optionallyfluorine-, chlorine-, bromine-, nitro-, cyano-, C₁-C₃-alkoxy-,C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-, C₁-C₃-halogenoalkylthio,C₁-C₃-alkyl- or C₁-C₃-halogenoalkyl-substituted phenyl, phenoxy orphenylthio.

[0230] R⁶ and R⁷ each particularly preferably represent independently ofone another hydrogen, respectively optionally fluorine- orchlorine-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl, respectively optionallyfluorine-, chlorine-, bromine-, C₁-C₅-halogenoalkyl-, C₁-C₅-alkyl- orC₁-C₅-alkoxy-substituted phenyl or benzyl, or particularly preferablyrepresent together an optionally C₁-C₄-alkyl-substituted C₃-C₆-alkyleneradical in which one methylene group is optionally replaced by oxygen orsulphur.

[0231] R¹³ particularly preferably represents hydrogen or respectivelyoptionally fluorine- or chlorine-substituted C₁-C₆-alkyl orC₁-C₆-alkoxy, optionally fluorine-, C₁-C₂-alkyl- orC₁-C₂-alkoxy-substituted C₃-C₇-cycloalkyl in which one methylene groupis optionally replaced by oxygen or sulphur, or particularly preferablyrepresents respectively optionally fluorine-, chlorine-, bromine-,C₁-C₅-alkyl-, C₁-C₅-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₃-alkyl or phenyl-C₁-C₂-alkyloxy.

[0232] R¹⁴ particularly preferably represents hydrogen or C₁-C₆-alkyl or

[0233] R¹³ and R¹⁴ together particularly preferably representC₄-C₆-alkanediyl.

[0234] R¹⁵ and R¹⁶ are identical or different and particularlypreferably represent C₁-C₄-alkyl or

[0235] R¹⁵ and R¹⁶ together particularly preferably represent aC₂-C₃-alkanediyl radical which is optionally substituted by C₁-C₄-alkylor optionally fluorine-, chlorine-, bromine-, C₁-C₂-alkyl-,C₁-C₂-halogenoalkyl-, C₁-C₂-alkoxy-, C₁-C₂-halogenoalkoxy-, nitro- orcyano-substituted phenyl.

[0236] V very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, propyl, isopropyl, tert-butyl,methoxy, ethoxy, propoxy or isopropoxy.

[0237] W very particularly preferably represents cyano, nitro, fluorine,chlorine, bromine, methyl, ethyl, propyl, butyl, isopropyl, isobutyl,tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy, phenyl or benzyloxy.

[0238] X very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl,tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano, nitro, phenyl or benzyloxy.

[0239] Y very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl,tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl,trifluoromethoxy, difluoromethoxy, cyano or nitro.

[0240] Z very particularly preferably represents fluorine, chlorine,bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert-butyl,methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano or nitro, or

[0241] Y and Z to-ether very particularly preferably representoptionally fluorine-, chlorine-, methyl-, ethyl-, propyl-, isopropyl-,methoxy-, ethoxy-, propoxy-, isopropoxy- or trifluoromethyl-substitutedC₃-C₄-alkanediyl in which two not directly adjacent members areoptionally replaced by oxygen, or

[0242] W and Z together very particularly preferably representoptionally fluorine-, chlorine-, methyl-, ethyl-, propyl-, isopropyl-,methoxy-, ethoxy-, propoxy-, isopropoxy- or trifluoromethyl-substitutedC₃-C₄-alkanediyl in which two not directly adjacent members areoptionally replaced by oxygen.

[0243] Het very particularly preferably represents one of the groups

[0244] A very particularly preferably represents hydrogen, respectivelyoptionally fluorine- or chlorine-substituted C₁-C₈-alkyl, C₂-C₄-alkenyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl orC₁-C₆-alkylthio-C₁-C₄-alkyl or optionally fluorine-, chlorine-, methyl-or methoxy-substituted C₃-C₆-cycloalkyl in which one or two not directlyadjacent methylene groups are optionally replaced by oxygen and/orsulphur, or very particularly preferably represents respectivelyoptionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-,isopropyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-,cyano- or nitro-substituted phenyl, pyridyl or benzyl.

[0245] B very particularly preferably represents hydrogen, C₁-C₈-alkylor C₁-C₄-alkoxy-C₁-C₂-alkyl or A, B and the carbon atom that they areattached to very particularly preferably represent C₃-C₈-cycloalkyl orC₅-C₈-cycloalkenyl where in each case one methylene group is optionallyreplaced by oxygen or sulphur and which are optionally substituted bymethyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, sec-butyl,tert-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, n-propoxy,isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio,ethylthio, fluorine, chlorine or phenyl or

[0246] A, B and the carbon atom that they are attached to veryparticularly preferably represent C₅-C₆-cycloalkyl which is substitutedby an alkylenediyl group optionally containing an oxygen or sulphuratom, or by an alkylenedioxy group forming a further five- orsix-membered ring with the carbon atom that it is attached to or

[0247] A, B and the carbon atom that they are attached to veryparticularly preferably represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenylin which two carbon atoms are connected by C₃-C₄-alkanediyl,C₃-C₄-alkenediyl or butadienediyl.

[0248] D very particularly preferably represents hydrogen, respectivelyoptionally fluorine- or chlorine-substituted C₁-C₈-alkyl C₃-C₄-alkenyl,C₃-C₄-alkinyl, C₁-C₆-alkoxy-C₂-C₄-alkyl, poly-C₁-C₄-alkoxy-C₂-C₄-alkyl,C₁-C₄-alkylthio-C₂-C₄-alkyl or C₃-C₆-cycloalkyl in which one or two notdirectly adjacent methylene groups are optionally replaced by oxygenand/or sulphur, or very particularly preferably represents respectivelyoptionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-,isopropyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-,cyano- or nitro-substituted phenyl, furanyl, pyridyl, thienyl or benzyl,or

[0249] A and D together very particularly preferably represent aC₃-C₅-alkanediyl or C₃-C₅-alkenediyl group where in each case onemethylene group is optionally replaced by oxygen or sulphur and whichare optionally substituted by fluorine, chlorine or respectivelyoptionally fluorine- or chlorine-substituted C₁-C₆-alkyl orC₁-C₄-alkoxy.

[0250] G very particularly preferably represents hydrogen (a) or one ofthe groups

[0251]  in which

[0252] E represents a metal ion equivalent or an ammonium ion,

[0253] L represents oxygen or sulphur and

[0254] M represents oxygen or sulphur.

[0255] R¹ very particularly preferably represents respectivelyoptionally fluorine- or chlorine-substituted C₁-C₁₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl, C₁-C₄-alkylthio-C₁-C₆-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or optionally fluorine-, chlorine-,methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-, tert-butyl-,methoxy-, ethoxy-, n-propoxy- or isopropoxy-substituted C₃-C₆-cycloalkylin which one or two not directly adjacent methylene groups areoptionally replaced by oxygen and/or sulphur,

[0256] optionally fluorine-, chlorine-, bromine-, cyano-, nitro-,methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-,methylsulphonyl- or ethylsulphonyl-substituted phenyl,

[0257] optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-,n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted benzyl, respectively optionally fluorine-,chlorine-, bromine-, methyl- or ethyl-substituted furanyl, thienyl orpyridyl,

[0258] optionally fluorine-, chlorine-, methyl- or ethyl-substitutedphenoxy-C₁-C₄-alkyl or

[0259] respectively optionally fluorine-, chlorine-, amino-, methyl- orethyl-substituted pyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl orthiazolyloxy-C ₁-C₄-alkyl.

[0260] R² very particularly preferably represents respectivelyoptionally fluorine- or chlorine-substituted C₁-C₁₄-alkyl,C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₂-C₆-alkyl orpoly-C₁-C₄-alkoxy-C₂-C₆-alkyl,

[0261] optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-,isopropyl- or methoxy-substituted C₃-C₆-cycloalkyl,

[0262] or respectively optionally fluorine-, chlorine-, cyano-, nitro-,methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl.

[0263] R³ very particularly preferably represents optionally fluorine-or chlorine-substituted methyl, ethyl, propyl, isopropyl, butyl,tert-butyl, or respectively optionally fluorine-, chlorine-, bromine-,methyl-, ethyl-, isopropyl-, tert-butyl-, methoxy-, ethoxy-,isopropoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl or benzyl.

[0264] R⁴ and R⁵ each very particularly preferably representindependently of one another respectively optionally fluorine- orchlorine-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino or C₁-C₄-alkylthio or respectively optionallyfluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl, phenoxy orphenylthio.

[0265] R⁶ and R⁷ each very particularly preferably representindependently of one another hydrogen, respectively optionally fluorine-or chlorine-substituted C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,C₃-C₄-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, respectively optionallyfluorine-, chlorine-, bromine-, methyl-, methoxy- ortrifluoromethyl-substituted phenyl or benzyl or together represent anoptionally methyl- or ethyl-substituted C₅-C₆-alkylene radical in whichone methylene group is optionally replaced by oxygen or sulphur.

[0266] Excluded are in each case the following compounds (disclosed inEP-0 528 156):

[0267] If, in the compounds of the formula (I-2), only the substituent Vof the substituents X, V, Y, Z and W represents hydrogen and X, Y, Z andW have a meaning different from hydrogen, then preference is given tosuch compounds of the formula (I-2) in which Z does not representhalogen.

[0268] The abovementioned definitions or illustrations of radicalsmentioned generally or in preferred ranges can be combined with eachother as desired, i.e. also between the respective ranges and preferredranges. They apply correspondingly to the final products and to theprecursors and intermediates.

[0269] For the purpose of the invention, preference is given tocompounds of the formula (I) in which there exists a combination of themeanings mentioned above as preferred (preferable).

[0270] For the purpose of the invention, particular preference is givento compounds of the formula (I) in which there exists a combination ofthe meanings mentioned above as particularly preferred.

[0271] For the purpose of the invention, very particular preference isgiven to the compounds of the formula (I) in which there exists acombination of the meanings mentioned above as very particularlypreferred.

[0272] Saturated or unsaturated hydrocarbon radicals such as alkyl oralkenyl can, as far as possible, in each case be straight-chain orbranched, also in combination with heteroatoms, e.g in alkoxy.

[0273] Optionally substituted radicals can be mono- or polysubstituted,it being possible in the case of polysubstitution for the substituentsto be identical or different.

[0274] Particular preference is given to compounds of the formula I-1 toI-3 in which

[0275] a) A, B and the carbon atom that they are attached to have themeanings mentioned as very particularly preferred and V representshydrogen,

[0276] b) A, B and the carbon atom that they are attached to have themeanings mentioned as very particularly preferred and V and Y representhydrogen.

[0277] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-1-a) may bespecifically mentioned:

TABLE 1 A B CH₃ H C₂H₅ H C₃H₇ H i-C₃H₇ H C₄H₉ H i-C₄H₉ H s-C₄H₉ H t-C₄H₉H CH₃ CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇ CH₃ C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃t-C₄H₉ CH₃ C₂H₅ C₂H₅ C₃H₇ C₃H₇

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —(CH₂)₂—O—(CH₂)₂——(CH₂)₂—S—(CH₂)₂— —CH₂—CHCH₃—(CH₂)₃— —(CH₂)₂—CHCH₃—(CH₂)₂——(CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂— —(CH₂)₂—CHi-C₃H₇—(CH₂)₂——(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂— —(CH₂)₂—CHOC₃H₇—(CH₂)₂——(CH₂)₂—CHOi-C₃H₇—(CH₂)₂— —(CH₂)₂—C(CH₃)₂—(CH₂)₂——(CH₂)₂—(CHCH₃)₂—(CH₂)₂—

[0278] Table 2: A and B are as defined in Table 1 with V=H; W=CH₃;X=CH₃; Y=H; Z=Cl

[0279] Table 3: A and B are as defined in Table 1 with V=H; W=CH₃;X=CH₃; Y=CH₃; Z=F

[0280] Table 4: A and B are as defined in Table 1 with V=H; W=CH₃;X=CH₃; Y=CH₃; Z=Cl

[0281] Table 5: A and B are as defined in Table 1 with V=H, W=CH₃;X=CH₃; Y=CH₃; Z=Br

[0282] Table 6: A and B are as defined in Table 1 with V=CH₃; W=CH₃;X=CH₃; Y=H; Z=CH₃

[0283] Table 7: A and B are as defined in Table 1 with V=CH₃; W=CH₃;X=H; Y=CH₃; Z=CH₃

[0284] Table 8: A and B are as defined in Table 1 with V=H; W=CH₃; X=C₃;Y=H; Z=Br

[0285] Table 9: A and B are as defined in Table 1 with V=H; W=Cl; X=Cl;Y=H; Z=Br

[0286] Table 10: A and B are as defined in Table 1 with V=H, W=Br; X=Br;Y, Z=—(CH₂)₃—

[0287] Table 11: A and B are as defined in Table 1 with V=H; W=CH₃;X=OCH₃; Y=H; Z=Br

[0288] Table 12: A and B are as defined in Table 1 with V=CH₃; W=CH₃;X=CH₃; Y=CH₃; Z=CH₃

[0289] Table 13: A and B are as defined in Table 1 with V=H; W=Cl; X=Cl;Y=Cl; Z=CH₃

[0290] Table 14: A and B are as defined in Table 1 with V=H; W=Br, X=Br;Y=Br; Z=CH₃

[0291] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-2-a) may bespecifically mentioned: TABLE 15

A B CH₃ H C₂H₅ H C₃H₇ H i-C₃H₇ H C₄H₉ H i-C₄H₉ H s-C₄H₉ H t-C₄H₉ H CH₃CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇ CH₃ C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃ t-C₄H₉CH₃ C₂H₅ C₂H₅ C₃H₇ C₃H₇

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —(CH₂)₂—O—(CH₂)₂——(CH₂)₂—S—(CH₂)₂— —CH₂—CHCH₃—(CH₂)₃— —(CH₂)₂—CHCH₃—(CH₂)₂——(CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂— —(CH₂)₂—CHi-C₃H₇—(CH₂)₂——(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂— —(CH₂)₂—CHOC₃H₇—(CH₂)₂——(CH₂)₂—CHOi-C₃H₇—(CH₂)₂— —(CH₂)₂—C(CH₃)₂—(CH₂)₂— —CH₂—(CHCH₃)₂—(CH₂)₂—

[0292] Table 16: A and B are as defined in Table 15 with V=H, W=CH₃;X=CH₃; Y=H; Z=Cl

[0293] Table 17: A and B are as defined in Table 15 with V=CH₃; W=CH₃;X=CH₃; Y=H; Z=CH₃

[0294] Table 18: A and B are as defined in Table 15 with V=CH₃, W=CH₃;X=H; Y=CH₃; Z=CH₃

[0295] Table 19: A and B are as defined in Table 15 with V=H, W=CH₃;X=CH₃; Y=H; Z=Br

[0296] Table 20: A and B are as defined in Table 15 with V=H, W=Cl,X=Cl, Y=H; Z=Br

[0297] Table 21: A and B are as defined in Table 15 with V=H; W=Br;X=Br; Y, Z=—(CH₃)₂—

[0298] Table 22: A and B are as defined in Table 15 with V=H; W=CH₃;X=OCH₃; Y=H; Z=Br

[0299] Table 23: A and B are as defined in Table 15 with V=CH₃; W=CH₃;X=CH₃; Y=CH₃; Z=CH₃

[0300] Table 24: A and B are as defined in Table 15 with V=H; W=Cl;X=Cl; Y=Cl; Z=CH₃

[0301] Table 25: A and B are as defined in Table 15 with V=H; W=Br;X=Br; Y=Br, Z=CH₃

[0302] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-3-a) may bespecifically mentioned: TABLE 26

A B CH₃ H C₂H₅ H C₃H₇ H i-C₃H₇ H C₄H₉ H i-C₄H₉ H s-C₄H₉ H t-C₄H₉ H CH₃CH₃ C₂H₅ CH₃ C₃H₇ CH₃ i-C₃H₇ CH₃ C₄H₉ CH₃ i-C₄H₉ CH₃ s-C₄H₉ CH₃ t-C₄H₉CH₃ C₂H₅ C₂H₅ C₃H₇ C₃H₇

CH₃

CH₃

CH₃ —(CH₂)₂— —(CH₂)₄— —(CH₂)₅— —(CH₂)₆— —(CH₂)₇— —(CH₂)₂—O—(CH₂)₂——(CH₂)₂—S—(CH₂)₂— —CH₂—CHCH₃—(CH₂)₃— —(CH₂)₂—CHCH₃—(CH₂)₂——(CH₂)₂—CHC₂H₅—(CH₂)₂— —(CH₂)₂—CHC₃H₇—(CH₂)₂— —(CH₂)₂—CHi-C₃H₇—(CH₂)₂——(CH₂)₂—CHOCH₃—(CH₂)₂— —(CH₂)₂—CHOC₂H₅—(CH₂)₂— —(CH₂)₂—CHOC₃H₇—(CH₂)₂——(CH₂)₂—CHOi-C₃H₇—(CH₂)₂— —(CH₂)₂—C(CH₃)₂—(CH₂)₂——(CH₂)₂—(CHCH₃)₂—(CH₂)₂—

[0303] Table 27: A and B are as defined in Table 26 with V=H; W=CH₃;X=CH₃; Y=H; Z=Cl

[0304] Table 28: A and B are as defined in Table 26 with V=H; W=CH₃;X=CH₃; Y=CH₃; Z=Cl

[0305] Table 29: A and B are as defined in Table 26 with V=H, W=CH₃;X=CH₃; Y=CH₃; Z=F

[0306] Table 30: A and B are as defined in Table 26 with V=H; W=CH₃;X=CH₃; Y=CH₃; Z=Br

[0307] Table 31: A and B are as defined in Table 26 with V=CH₃; W=CH₃;X=CH₃; Y=H; Z=CH₃

[0308] Table 32: A and B are as defined in Table 26 with V=CH₃; W=CH₃;X=H; Y=CH₃; Z=CH₃

[0309] Table 33: A and B are as defined in Table 26 with V=H; W=CH₃;X=CH₃; Y=H; Z=Br

[0310] Table 34: A and B are as defined in Table 26 with V=H; W=Cl;X=Cl; Y=H; Z=Br

[0311] Table 35: A and B are as defined in Table 26 with V=H; W=Br;X=Br; Y, Z=—(CH₂)₃—

[0312] Table 36: A and B are as defined in Table 26 with V=H; W=CH₃;X=OCH₃; Y=H; Z=Br

[0313] Table 37: A and B are as defined in Table 26 with V=CH₃; W=CH₃;X=CH₃; Y=CH₃; Z=CH₃

[0314] Table 38: A and B are as defined in Table 26 with V=H; W=Cl,X=Cl; Y=Cl; Z=CH₃

[0315] Table 39: A and B are as defined in Table 26 with V=H; W=Br;X=Br; Y=Br; Z=CH₃

[0316] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-4-a) may bespecifically mentioned: TABLE 40

A D H CH₃ H C(CH₃)₃ H C(CH₃)₂CH₂Cl CH₃ CH₃ CH₃ CH₂CHCH₃CH₂CH₃ HCH═C(CH₃)₂ CH₃

CH₃

CH₃

CH₃

CH₃

CH₃ H

CH₃

CH₃

CH₃

CH₃

H

CH₃ C₅H₉ CH₃ C₃H₅ H C₃H₄Cl (CH₂)₃ (CH₂)₄ C(CH₃)₂OC(CH₃)₂

[0317] Table 41: A and D are as defined in Table 40 with V=H; W=CH₃;X=CH₃; Y=H; Z=Cl

[0318] Table 42: A and D are as defined in Table 40 with V=H; W=CH₃;X=CH₃; Y=CH₃; Z=Cl

[0319] Table 43: A and D are as defined in Table 40 with V=H; W=CH₃;X=CH₃; Y=CH₃; Z=F

[0320] Table 44: A and D are as defined in Table 40 with V=H; W=CH₃;X=CH₃; Y=CH₃; Z=Br

[0321] Table 45: A and D are as defined in Table 40 with V=CH₃; W=CH₃;X=CH₃; Y=H; Z=CH₃

[0322] Table 46: A and P are as defined in Table 40 with V=CH₃; W=CH₃;X=H; Y=CH₃; Z=CH₃

[0323] Table 47: A and D are as defined in Table 40 with V=H; W=CH₃;X=CH₃; Y=H; Z=Br

[0324] Table 48: A and D are as defined in Table 40 with V=H; W=Cl;X=Cl; Y=H, Z=Br

[0325] Table 49: A and D are as defined in Table 40 with V=H; W=Br,X=Br; Y, Z=—(CH₂)₃—

[0326] Table 50: A and D are as defined in Table 40 with V=H, W=CH₃;X=OCH₃; Y=H; Z=Br

[0327] Table 51: A and D are as defined in Table 40 with V=CH; W=CH₃;X=CH₃; Y=CH₃; Z=CH₃

[0328] Table 52: A and D are as defined in Table 40 with V=H; W=Cl;X=Cl; Y=Cl; Z=CH₃

[0329] In addition to the compounds mentioned in the PreparationExamples, the following compounds of the formula (I-5-a) may bespecifically mentioned: TABLE 54

A CH₃ CH(CH₃)₂

[0330] Table 55: A is as defined in Table 54 with V=H, W=CH₃; X=CH₃;Y=H; Z=Cl

[0331] Table 56: A is as defined in Table 54 with V=H; W=CH₃; X=CH₃;Y=CH₃; Z=Cl

[0332] If according to process (A) ethylN-[(3,4-dichloro-2,6-dimethyl)-phenylacetyl]-1-amino-4-ethyl-cyclohexane-carboxylateis used as starting material, the course of the process according to theinvention can be represented by the following reaction scheme:

[0333] If according to process (B) ethylO-[(2,5-dichloro-6-methyl)-phenylacetyl]hydroxyacetate is used, thecourse of the process according to the invention can be represented bythe following reaction scheme:

[0334] If according to process (C) ethyl2-[(2-chloro-4,5,6-trimethyl)-phenyl]-4-(4-methoxy)-benzylmercapto-4-methyl-3-oxo-valerateis used, the course of the process according to the invention can berepresented by the following reaction scheme:

[0335] If, for example, according to process (D) chlorocarbonyl2-[(3,4-dichloro-2,6-dimethyl)-phenyl]ketene and acetone are used asstarting materials, the course of the process according to the inventioncan be represented by the following reaction scheme:

[0336] If, for example, according to process (E) chlorocarbonyl2-[(2,3,4,6-tetramethyl)-phenyl] ketene and thiobenzamide are used asstarting materials, the course of the process according to the inventioncan be represented by the following reaction scheme.

[0337] If according to process (Fα)3-[(2,5-dichloro-4,6-dimethyl)-phenyl]-5,5-dimethyl-pyrrolidine-2,4-dioneand pivaloyl chloride are used as starting materials, the course of theprocess according to the invention can be represented by the followingreaction scheme:

[0338] If according to process (F) (variant β)3-[(2,3-dichloro)-phenyl]-4-hydroxy-5-phenyl-Δ³-dihydrofuran-2-one andacetic anhydride are used as starting materials, the course of theprocess according to the invention can be represented by the followingreaction scheme:

[0339] If according to process (G)8-[(2,4-dichloro-3-methyl)-phenyl]-5,5-pentamethylene-pyrrolidine-2,4-dioneand ethoxyethyl chloroformate are used as starting materials, the courseof the process according to the invention can be represented by thefollowing reaction scheme.

[0340] If according to the process (H), (variant α)3-[(2,6-dibromo-3,4-dimethyl)-phenyl] -4-hydroxy-6-(3-pyridyl)-pyroneand methyl chloromonothioformate are used as starting materials, thecourse of the reaction can be represented in the following manner:

[0341] If according to process (H), (variant β)5-[(3-chloro-2,6-dimethyl)-phenyl]-6-hydroxy-2-(4-chlorophenyl)-thiazin-4-one,carbon disulphide and methyl iodide are used as starting materials, thecourse of the reaction can be represented as follows:

[0342] If according to process (I)2-[(2,3,4,6-tetramethyl)-phenyl]-5,5-[(3-methyl)pentamethylene]-pyrrolidine-2,4-dione and methanesulphonyl chloride are used asstarting materials, the course of the reaction can be represented by thefollowing reaction scheme:

[0343] If according to process (J)2-[(2-chloro-5,6-dimethyl)-phenyl]-4-hydroxy-5-methyl-6-(2-pyridyl)-pyrone and 2,2,2-trifluoroethyl chloromethanethio-phosphonate are usedas starting materials, the course of the reaction can be represented bythe following reaction scheme:

[0344] If according to process (K)3-[(2,4,5-trichloro)-6-methylphenyl]-5-cyclopropyl-5-methyl-pyrrolidine-2,4-dioneand NaOH are used as components, the course of the process according tothe invention can be represented by the following reaction scheme.

[0345] If according to process (L) (variant α)3-[(2,6-dichloro-4-bromo-3-methyl)-phenyl]-4-hydroxy-5,5-tetramethylene-Δ³-dihydro-furan-2-one and ethylisocyanate are used as starting materials, the course of the reactioncan be represented by the following reaction scheme:

[0346] If according to process (L) (variant β)3-[(2-chloro-5,6-dimethyl)-phenyl]-5-methyl-pyrrolidine-2,4-dione anddimethylcarbamoyl chloride are used as starting materials, the course ofthe reaction can be represented by the following scheme:

[0347] The compounds of the formula (II)

[0348] in which

[0349] A, B, V, W, X, Y, Z and R⁸ have the meanings given above,

[0350] needed as starting substances in process (A) according to theinvention are novel.

[0351] The acylamino acid esters of the formula (II) are obtained, forexample, when amino acid derivatives of the formula (XIX)

[0352] in which

[0353] A, B and R⁸ are each as defined above,

[0354] are acylated using substituted phenylacetyl halides of theformula (XX)

[0355] in which

[0356] V, W, X, Y and Z are each as defined above and

[0357] Hal represents chlorine or bromine,

[0358] (Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem.6, 341-5, 1968)

[0359] or when acylamino acids of the formula (XXI)

[0360] in which

[0361] A, B, V, W, X, Y and Z are each as defined above,

[0362] are esterified (Chem. Ind. (London) 1568 (1968)).

[0363] The compounds of the formula (XXI)

[0364] in which

[0365] A, B, V, W, X, Y and Z are each as defined above,

[0366] are novel.

[0367] The compounds of the formula (XXI) are obtained when amino acidsof the formula (XXII)

[0368] in which

[0369] A and B are each defined as above,

[0370] are acylated using substituted phenylacetyl halides of theformula (XX)

[0371] in which

[0372] V, W, X, Y and Z are each as defined above and

[0373] Hal represents chlorine or bromine,

[0374] according to Schotten-Baumann (Organikum, VEB Deutscher Verlagder Wissenschaften, Berlin 1977, p. 505).

[0375] Some of the compounds of the formula (XX) are novel and can beprepared by known methods.

[0376] The compounds of the formula (XX) are obtained, for example, byreacting substituted phenylacetic acids of the formula (XXIII)

[0377] in which

[0378] V, W, X, Y and Z are each as defined above,

[0379] with halogenating agents (e.g. thionyl chloride, thionyl bromide,oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromideor phosphorus pentachloride), if appropriate in the presence of adiluent (e.g. optionally chlorinated aliphatic or aromatic hydrocarbonssuch as toluene or methylene chloride) at temperatures from −20° C. to150° C., preferably from −10° C. to 100° C.

[0380] Some of the compounds of the formula (XXIII) are novel, they canbe prepared by methods known from the literature (Organikum 15thedition, p. 533, VEB Deutscher Verlag der Wissenschaften, Berlin 1977).The compounds of the formula (XXIII) are obtained, for example, byhydrolysing substituted phenylacetic acid esters of the formula (XXIV)

[0381] in which

[0382] V, W, X, Y, Z and R⁸ are each as defined above,

[0383] at temperatures between 0° C. and 150° C., preferably between 20°C. and 100° C., in the presence of an acid (e.g. of an inorganic acidsuch as hydrochloric acid) or of a base (e.g. of an alkali metalhydroxide such as sodium or potassium hydroxide) and, if appropriate, ofa diluent (e.g. of an aqueous alcohol such as methanol or ethanol).

[0384] Some of the compounds of the formula (XXIV) are novel, they canbe prepared by methods known in principle.

[0385] The compounds of the formula (XXIV) are obtained, for example, byreacting substituted 1,1,1-trichloro-2-phenylethanes of the formula(XXV)

[0386] in which

[0387] V, W, X, Y and Z are each as defined above,

[0388] first with alkoxides (e.g. alkali metal alkoxides such as sodiummethoxide or sodium ethoxide) in the presence of a diluent (e.g. thealcohol derived from the alkoxide) at temperatures between 0° C. and150° C., preferably between 20° C. and 120° C., and then reacting withan acid (preferably an inorganic acid, e.g. sulphuric acid) attemperatures between −20° C. and 150° C., preferably 0° C. and 100° C.(cf. DE-33 14 249).

[0389] Some of the compounds of the formula (XXV) are novel, they can beprepared by methods known in principle.

[0390] The compounds of the formula (XXV) are obtained, for example,when anilines of the formula (XXVI)

[0391] in which

[0392] V, W, X, Y and Z are each as defined above,

[0393] are reacted with vinylidene chloride (CH₂=CCl₂) in the presenceof an alkyl nitrite of the formula (XXVII)

R²¹—ONO   (XXVII)

[0394] in which

[0395] R²¹ represents alkyl, preferably C₁-C₆-alkyl,

[0396] in the presence of copper(II) chloride and if appropriate in thepresence of a diluent (e.g. of an aliphatic nitrile such asacetonitrile) at a temperature of −20° C. to 80° C., preferably 0° C. to60° C.

[0397] Some of the compounds of the formula (XXVI) are known compounds,or they can be prepared by methods known in principle. The compounds ofthe formula (XXVII) are known compounds of organic chemistry. Copper(II)chloride and vinylidene chloride have long been known and arecommercially available.

[0398] The compounds of the formulae (XIX) and (XXII) are known in somecases and/or can be prepared by known processes (see, for example,Compagnon, Miocque, Ann. Chim. (Paris) [14]5, p. 11-22, 23-27 (1970)).

[0399] The substituted cyclic aminocarboxylic acids of the formula(XXIIa), in which A and B form a ring, are in general obtainable by theBucherer-Bergs synthesis or by the Strecker synthesis and are in eachcase obtained here in different isomeric forms. Thus, according to theconditions of the Bucherer-Bergs synthesis mainly the isomers (in thefollowing designated as β for the sake of simplicity) in which theradicals R and the carboxyl group are equatorial are obtained, whileaccording to the conditions of the Strecker synthesis mainly the isomers(in the following designated as α for the sake of simplicity) areobtained in which the amino group and the radicals R are equatorial.

[0400] (L. Munday, J. Chem. Soc. 4372 (1961); J. T. Eward, C.Jitrangeri, Can. J. Chem. 53, 3339 (1975)).

[0401] Furthermore, the starting materials of the formula (II)

[0402] in which

[0403] A, B, V, W X, Y, Z and R⁸ are each as defined above,

[0404] used in the above process (A) can be prepared by reactingaminonitriles of the formula (XXVIII)

[0405] in which

[0406] A and B are as defined above,

[0407] with substituted phenylacetyl halides of the formula (XX)

[0408] in which

[0409] V, W, X, Y, Z and Hal are each as defined above,

[0410] to give compounds of the formula (XXIX)

[0411] in which

[0412] A, B, V, W X, Y and Z are each as defined above,

[0413] and these are then subjected to an acidic alcoholysis.

[0414] The compounds of the formula (XXIX) are also novel.

[0415] The compounds of the formula (III)

[0416] in which

[0417] A, B, V, W, X, Y, Z and R⁸ are each as defined above,

[0418] needed as starting materials in process (B) according to theinvention are novel.

[0419] They can be prepared in a simple manner by methods known inprinciple.

[0420] The compounds of the formula (III) are obtained, for example,when 2-hydroxycarboxylic acid esters of the formula (XXX)

[0421] in which

[0422] A, B and R⁸ are each as defined above,

[0423] are acylated using substituted phenylacetyl halides of theformula (XX)

[0424] in which

[0425] V, W, X, Y, Z and Hal are each as defined above,

[0426] (Chem. Reviews 52, 237-416 (1953)).

[0427] Furthermore, compounds of the formula (III) are obtained whensubstituted phenylacetic acids of the formula (XXIII)

[0428] in which

[0429] V, W, X, Y and Z are each as defined above,

[0430] are alkylated using α-halogenocarboxylic acid esters of theformula (XXXI)

[0431] in which

[0432] A, B and R⁸ are each as defined above and

[0433] Hal represents chlorine or bromine.

[0434] The compounds of the formula (XXXI) are commercially available.

[0435] The compounds of the formula (IV)

[0436] in which

[0437] A, B, T, V, W, X, Y, Z and R⁸ are each as defined above,

[0438] needed as starting substances in the above process (C) are novel.

[0439] They can be prepared by methods known in principle.

[0440] The compounds of the formula (IV) are obtained, for example, whensubstituted phenylacetic acid esters of the formula (XXIV)

[0441] in which

[0442] V, W, X, Y, R⁸ and Z are each as defined above,

[0443] are acylated using 2-benzylthio-carbonyl halides of the formula(XXXII)

[0444] in which

[0445] A, B and T are each as defined above and

[0446] Hal represents halogen (in particular chlorine or bromine),

[0447] in the presence of strong bases (see, for example, M. S.Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc. Chem. Commun.,(1987), 1228).

[0448] The benzylthio-carbonyl halides of the formula (XXXII) are knownin some cases and/or can be prepared by known methods (J. Antibiotics(1983), 26, 1589).

[0449] The halogenocarbonylketenes of the formula (VI) needed asstarting materials in process (D) are novel. They can be prepared in asimple manner by methods known in principle (cf., for example, Org Prep.Proced. Int., 7, (4), 155-158, 1975 and DE 1 945 703). The compounds ofthe formula (VI)

[0450] in which

[0451] V, W, X, Y and Z are each as defined above and

[0452] Hal represents chlorine or bromine,

[0453] are obtained when substituted phenylmalonic acids of the formula(XXXIII)

[0454] in which

[0455] V, W, X, Y and Z are each as defined above,

[0456] are reacted with acid halides, for example thionyl chloride,phosphorus(V) chloride, phosphorus(III) chloride, oxalyl chloride,phosgene or thionyl bromide, if appropriate in the presence ofcatalysts, for example diethylformamide, methylsterylformamide ortriphenylphosphine and if appropriate in the presence of bases, e.g.pyridine or triethylamine, at a temperature between −20° C. and 200° C.,preferably between 0° C. and 150° C.

[0457] The substituted phenylmalonic acids of the formula (XXXIII) arenovel. However, they can be prepared by known processes in a simplemanner (cf., for example Organikum, VEB Deutscher Verlag derWissenschaften, Berlin 1977, p. 517 ff), for example by saponificationof substituted phenylmalonic esters of the formula (XXXIV)

[0458] in which

[0459] V, W, X, Y, Z and R⁸ are each as defined above.

[0460] The carbonyl compounds of the formula (V) or their silyl enolethers of the formula (Va)

[0461] in which

[0462] A, D and R^(8′) are each as defined above,

[0463] needed as starting materials for process (E) according to theinvention are compounds which are commercially available, generallyknown or accessible by known processes.

[0464] The preparation of the ketene acid chlorides of the formula (VI)needed as starting materials for carrying out process (E) according tothe invention has already been described for process (D) according tothe invention. The thioamides of the formula (VII)

[0465] in which

[0466] A is as defined above,

[0467] needed for carrying out process (E) according to the inventionare compounds which are generally known in organic chemistry.

[0468] The malonic acid esters of the formula (XXXIV)

[0469] in which

[0470] R⁸, V, W, X, Y and Z are each as defined above,

[0471] are novel and can be prepared by generally known methods oforganic chemistry (cf., for example, Tetrahedron Lett. 27, 2763 (1986)and Organikum VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p.587 ff.).

[0472] The acid halides of the formula (VIII), carboxylic anhydrides ofthe formula (IX), chloroformic acid esters or chloroformic acidthioesters of the formula (X), chloromonothioformic acid esters orchlorodithioformic acid esters of the formula (XI), alkyl halides of theformula (XII), sulphonyl chlorides of the formula (XIII), phosphoruscompounds of the formula (XIV) and metal hydroxides, metal alkoxides oramines of the formula (XV) and (XVI) and isocyanates of the formula(XVII) and carbamoyl chlorides of the formula (XVIII) additionallyneeded as starting substances for carrying out processes (F), (G), (H),(I), (J), (K) and (L) according to the invention are generally knowncompounds of organic or inorganic chemistry

[0473] The compounds of the formulae (V), (VII) to (XVIII), (XIX),(XXII), (XXVIII), (XXX), (XXXI), (XXXII), (XXXIII) and (XXXIV) aremoreover disclosed in the patent applications cited at the outset and/orcan be prepared by the methods given there

[0474] Process (A) is characterized in that compounds of the formula(II), in which A, B, V, W, X, Y, Z and R⁸ are each as defined above, aresubjected to an intra-molecular condensation in the presence of adiluent and in the presence of a base.

[0475] Diluents employed in process (A) according to the invention canbe all organic solvents which are inert to the reaction participants.Those preferably utilizable are hydrocarbons, such as toluene andxylene, further ethers, such as dibutyl ether, tetrahydrofuran, dioxane,glycol dimethyl ether and diglycol dimethyl ether, additionally polarsolvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone, and also alcohols such as methanol, ethanol,propanol, iso-propanol, butanol, iso-butanol and tert-butanol.

[0476] Suitable bases (deprotonating agents) employed in carrying outprocess (A) according to the invention can be all customary protonacceptors. Those preferably utilizable are alkali metal and alkalineearth metal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, each of which can also beemployed in the presence of phase-transfer catalysts, e.gtriethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium orpotassium can furthermore be used. Alkali metal and alkaline earth metalamides and hydrides, such as sodium amide, sodium hydride and calciumhydride, and additionally also alkali metal alkoxides, such as sodiummethoxide, sodium ethoxide and potassium tert-butoxide can further beemployed.

[0477] When carrying out process (A) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −50° C. and250° C., preferably between −30° C. and 150° C.

[0478] Process (A) according to the invention is in general carried outunder atmospheric pressure.

[0479] When carrying out process (A) according to the invention, thereaction component of the formula (II) and the deprotonating base are ingeneral employed in equimolar to approximately double equimolar amounts.However, it is also possible to use one component or the other in arelatively large excess (up to 3 mol)

[0480] Process (B) is characterized in that compounds of the formula(III), in which A, B, V, W, X, Y, Z and R⁸ are each as defined above,are condensed intramolecularly in the presence of a diluent and in thepresence of a base.

[0481] The diluents employed in process (B) according to the inventioncan be all organic solvents which are inert to the reactionparticipants. Those preferably utilizable are hydrocarbons, such astoluene and xylene, furthermore ethers, such as dibutyl ether,tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethylether, and additionally polar solvents, such as dimethyl sulphoxide,sulpholane, dimethylformamide and N-methyl-pyrrolidone. Alcohols such asmethanol, ethanol, propanol, iso-propanol, butanol, iso-butanol andtert-butanol can furthermore be employed.

[0482] The bases (deprotonating agents) employed in carrying out process(B) according to the invention can be all customary proton acceptors.Those preferably utilizable are alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, each of which can also be employed inthe presence of phase-transfer catalysts, e.g. triethylbenzylammoniumchloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium orpotassium can furthermore be used. Alkali metal and alkaline earth metalamides and hydrides, such as sodium amide, sodium hydride and calciumhydride, and additionally also alkali metal alkoxides, such as sodiummethoxide, sodium ethoxide and potassium tert-butoxide can additionallyalso be employed.

[0483] When carrying out process (B) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −50° C. and250° C., preferably between −30° C. and 150° C.

[0484] Process (B) according to the invention is in general carried outunder atmospheric pressure.

[0485] When carrying out process (B) according to the invention, thereaction components of the formula (III) and the deprotonating bases arein general employed in approximately equimolar amounts. However, it isalso possible to use one component or the other in a relatively largeexcess (up to 3 mol).

[0486] Process (C) is characterized in that compounds of the formula(IV), in which A, B, T, V, W, X, Y, Z and R⁸ are each as defined above,are cyclized intra-molecularly in the presence of an acid and ifappropriate in the presence of a diluent.

[0487] Diluents which can be employed in process (C) according to theinvention are all organic solvents which are inert to the reactionparticipants. Those preferably utilizable are hydrocarbons, such astoluene and xylene, further halogenated hydrocarbons such asdichloromethane, chloroform, ethylene chloride, chlorobenzene,dichlorobenzene, additionally polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone.Alcohols such as methanol, ethanol, propanol, iso-propanol, butanol,isobutanol, tert-butanol can furthermore be employed.

[0488] The acid employed can optionally also be used as a diluent.

[0489] Acids which can be employed in process (C) according to theinvention are all customary inorganic and organic acids, e.g. hydrohalicacids, sulphuric acid, alkyl-, aryl- and haloalkylsulphonic acids;halogenated alkylcarboxylic acids, e.g. trifluoroacetic acid, are usedin particular.

[0490] When carrying out process (C) according to the invention, thereaction temperature can be varied within a relatively wide range. Ingeneral, the reaction is carried out at temperatures between −30° C. and250° C., preferably between 0° C. and 150° C.

[0491] Process (C) according to the invention is in general carried outunder atmospheric pressure

[0492] When carrying out process (C) according to the invention, thereaction components of the formulae (IV) and the acid are employed, forexample, in equimolar amounts. However, it is optionally also possibleto employ the acid in catalytic amounts.

[0493] Process (D) according to the invention is characterized in thatcarbonyl compounds of the formula (V) or their silyl enol ethers of theformula (Va) in which A and B are each as defined above are reacted withketene acid halides of the formula (VI) in which V, W, X, Y and Z areeach as defined above, if appropriate in the presence of a diluent andif appropriate in the presence of an acid acceptor.

[0494] Diluents which can be employed in process (D) according to theinvention are all organic solvents which are inert to the reactionparticipants. Those preferably utilizable are hydrocarbons, such aso-dichlorobenzene, tetralin, toluene and xylene, furthermore ethers,such as dibutyl ether, glycol dimethyl ether and diglycol dimethylether, and additionally polar solvents, such as dimethyl sulphoxide,sulpholane, dimethylformamide or N-methyl-pyrrolidone.

[0495] Acid acceptors which can be used when carrying out process (D)according to the invention are all customary acid acceptors.

[0496] Those preferably utilizable are tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig base orN,N-dimethyl-aniline.

[0497] When carrying out process (D) according to the invention, thereaction temperature can be varied within a relatively wide range. Thereaction is expediently carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 220° C.

[0498] Process (D) according to the invention is preferably carried outunder atmospheric pressure.

[0499] When carrying out process (D) according to the invention, thereaction components of the formulae (V) and (VI) and, if appropriate,the acid acceptor are in general employed in approximately equimolaramounts. However, it is also possible to use one component or the otherin a relatively large excess (up to 5 mol).

[0500] Process (E) according to the invention is characterized in thatthioamides of the formula (VII) in which A is as defined above arereacted with ketene acid halides of the formula (VI), in which V, W, X,Y and Z are as defined above, if appropriate in the presence of adiluent and if appropriate in the presence of an acid acceptor.

[0501] Diluents which can be employed in process variant (E) accordingto the invention are all inert organic solvents. Those preferablyutilizable are hydrocarbons, such as o-dichlorobenzene, tetralin,toluene and xylene, furthermore ethers, such as dibutyl ether, glycoldimethyl ether and diglycol dimethyl ether, and additionally polarsolvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide andN-methyl-pyrrolidone.

[0502] Acid acceptors which can be used in carrying out process (E)according to the invention are all customary acid acceptors.

[0503] Those preferably utilizable are tertiary amines, such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecane (DBU), diazabicyclononene (DBN), Hünig base andN,N-dimethyl-aniline.

[0504] When carrying out process (E) according to the invention, thereaction temperature can be varied within a relatively wide range. Thereaction is expediently carried out at temperatures between 0° C. and250° C., preferably between 20° C. and 220° C.

[0505] Process (E) according to the invention is expediently carried outunder atmospheric pressure.

[0506] When carrying out process (E) according to the invention, thereaction components of the formulae (VII) and (VI) and, if appropriate,the acid acceptors are in general employed in approximately equimolaramounts. However, it is also possible to use one component or the otherin a relatively large excess (up to 5 mol)

[0507] Process (Fα) is characterized in that compounds of the formulae(I-1-a) to (I-5-a) are in each case reacted with carboxylic acid halidesof the formula (VIII), if appropriate in the presence of a diluent andif appropriate in the presence of an acid-binding agent

[0508] Diluents which can be employed in process (Fα) according to theinvention are all solvents inert to the acid halides. Those preferablyutilizable are hydrocarbons, such as benzine, benzene, toluene, xyleneand tetralin, furthermore halogenohydrocarbons, such as methylenechloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, additionally ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, moreover carboxylic acid esters, such asethyl acetate, and also strongly polar solvents, such asdimethylformamide, dimethyl sulphoxide and sulpholane. If the stabilityto hydrolysis of the acid halide permits, the reaction can also becarried out in the presence of water.

[0509] In the reaction by process (Fα) according to the invention,suitable acid-binding agents are all customary acid acceptors. Thosepreferably utilizable are tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium and calciumoxide, additionally alkali metal and alkaline earth metal carbonates,such as sodium carbonate, potassium carbonate and calcium carbonate andalso alkali metal hydroxides such as sodium hydroxide and potassiumhydroxide.

[0510] In process (Fα) according to the invention, the reactiontemperature can be varied within a relatively wide range. In general,the reaction is carried out at temperatures between −20° C. and +150°C., preferably between 0° C. and 100° C.

[0511] When carrying out process (Fα) according to the invention, thestarting substances of the formulae (I-1-a) to (I-5-a) and thecarboxylic acid halide of the formula (VIII) are in general each used inapproximately equivalent amounts. However, it is also possible to employthe carboxylic acid halide in a relatively large excess (up to 5 mol).Work-up is carried out according to customary methods.

[0512] Process (Fβ) is characterized in that compounds of the formulae(I-1-a) to (I-5-a) are each reacted with carboxylic anhydrides of theformula (IX), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid-binding agent

[0513] Diluents which can be used in process (Fβ) according to theinvention are preferably those diluents which are also suitable whenusing acid halides. Otherwise, a carboxylic anhydride employed in excesscan also simultaneously function as diluent.

[0514] Possible acid-binding agents optionally added in process (Fβ) arepreferably those acid-binding agents which are also suitable when usingacid halides.

[0515] The reaction temperature in process (Fβ) according to theinvention can be varied within a relatively wide range. In general, thereaction is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

[0516] When carrying out process (Fβ) according to the invention, thestarting substances of the formulae (I-1-a) to (I-5-a) and thecarboxylic anhydride of the formula (XI) are in general used inapproximately equivalent amounts in each case. However, it is alsopossible to employ the carboxylic anhydride in a relatively large excess(up to 5 mol). Work-up is carried out according to customary methods.

[0517] In general, a procedure is used in which diluent and carboxylicanhydride present in excess and also the resulting carboxylic acid areremoved by distillation or by washing with an organic solvent or withwater.

[0518] Process (G) is characterized in that compounds of the formulae(I-1-a) to (I-5-a) are each reacted with chloroformic acid esters orchloroformic acid thioesters of the formula (X), if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.

[0519] Possible acid-binding agents in process (G) according to theinvention are all customary acid acceptors Those preferably utilizableare tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBA,Hünig base and N,N-dimethylaniline, furthermore alkaline earth metaloxides, such as magnesium and calcium oxide, additionally alkali metaland alkaline earth metal carbonates, such as sodium carbonate, potassiumcarbonate and calcium carbonate and also alkali metal hydroxides such assodium hydroxide and potassium hydroxide.

[0520] Diluents which can be employed in process (G) according to theinvention are all solvents which are inert to the chloroformic acidesters or chloroformic acid thioesters. Those preferably utilizable arehydrocarbons, such as benzine, benzene, toluene, xylene and tetralin,further halogenohydrocarbons, such as methylene chloride, chloroform,carbon tetrachloride, chlorobenzene and o-dichlorobenzene, additionallyketones, such as acetone and methyl isopropyl ketone, furthermoreethers, such as diethyl ether, tetrahydrofuran and dioxane, moreovercarboxylic acid esters, such as ethyl acetate, furthermore nitriles,such as acetonitrile, and also strongly polar solvents, such asdimethylformamide, dimethyl sulphoxide and sulpholane.

[0521] When carrying out process (G) according to the invention, thereaction temperature can be varied within a relatively wide range. Thereaction temperature is in general between −20° C. and +100° C.,preferably between 0° C. and 50° C.

[0522] Process (G) according to the invention is in general carried outunder atmospheric pressure.

[0523] When carrying out process (G) according to the invention, thestarting substances of the formulae (I-1-a) to (I-5-a) and theapproporiate chloroformic acid esters or chloroformic acid thioesters ofthe formula (X) are in general each used in approximately equivalentamounts. However, it is also possible to employ one component or theother in a relatively large excess (up to 2 mol). Work-up is carried outaccording to customary methods. In general, a procedure is used in whichprecipitated salts which are deposited are removed and the reactionmixture which remains is concentrated by stripping off the diluent.

[0524] Process (H) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are each reacted with (Hα)compounds of the formula (XI) in the presence of a diluent and ifappropriate in the presence of an acid-binding agent or (Hβ) carbondisulphide and then with alkyl halides of the formula (XII), ifappropriate in the presence of a diluent and if appropriate in thepresence of a base.

[0525] In preparation process (Hα), about 1 mol of chloromonothioformicacid ester or chlorodithioformic acid ester of the formula (XI) isreacted at 0 to 120° C., preferably at 20 to 60° C., per mole ofstarting compound of the formulae (I-1-a) to (I-5-a).

[0526] Possible diluents optionally added are all inert polar organicsolvents, such as ethers, amides, sulphones, sulphoxides, but alsohalogenoalkanes.

[0527] Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide ormethylene chloride are preferably employed.

[0528] If, in a preferred embodiment, the enolate salt of the compounds(I-1-a) to (I-5-a) is prepared by addition of strong deprotonatingagents, e.g. sodium hydride or potassium tertiary butoxide, the furtheraddition of acid-binding agents can be dispensed with

[0529] If acid-binding agents are employed, customary inorganic ororganic bases are suitable; sodium hydroxide, sodium carbonate,potassium carbonate, pyridine and triethylamine may be mentioned by wayof example.

[0530] The reaction can be carried out at atmospheric pressure or atelevated pressure; it is preferably carried out at normal pressure.Work-up takes place according to customary methods.

[0531] In preparation process (Hβ), the equimolar amount or an excess ofcarbon disulphide is in each case added per mole of starting compoundsof the formulae (I-1l-a) to (I-5-a). The reaction is in this casepreferably carried out at temperatures from 0 to 50° C. and inparticular at 20 to 30° C.

[0532] Often it is expedient first to prepare the corresponding saltfrom the compounds of the formulae (I-1-a) to (I-5-a) by addition of abase (e.g. potassium tertiary butoxide or sodium hydride). The compounds(I-1-a) to (I-5-a) are each reacted with carbon disulphide until theformation of the intermediate compound is complete, e.g. after stirringat room temperature for several hours.

[0533] Bases which can be employed in process (Hβ) are all customaryproton acceptors. Those preferably utilizable are alkali metal hydrides,alkali metal alkoxides, alkali metal or alkaline earth metal carbonatesor hydrogen carbonates or nitrogen bases. Those which may be mentioned,for example, are sodium hydride, sodium methoxide, sodium hydroxide,calcium hydroxide, potassium carbonate, sodium hydrogen carbonate,triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline,diazabicyclooctane (DABCO), diazabicyclononene (DBN) anddiazabicycloundecene (DBU).

[0534] Diluents which can be used in this process are all customarysolvents.

[0535] Those preferably utilizable are aromatic hydrocarbons such asbenzene or toluene, alcohols such as methanol, ethanol, isopropanol orethylene glycol, nitriles such as acetonitrile, ethers such astetrahydrofuran or dioxane, amides such as dimethylformamide or otherpolar solvents such as dimethyl sulphoxide or sulpholane.

[0536] Further reaction with the alkyl halide of the formula (XII) ispreferably carried out at 0 to 70° C. and in particular at 20 to 50° C.In this case, at least the equimolar amount of alkyl halide is employed.

[0537] The reaction is carried out at atmospheric pressure or atelevated pressure, preferably at atmospheric pressure.

[0538] Work-up is in turn carried out according to customary methods.

[0539] Process (I) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are each reacted withsulphonyl chlorides of the formula (XIII), if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.

[0540] In preparation process (I), about 1 mol of sulphonyl chloride ofthe formula (XIII) is reacted at −20 to 150° C., preferably at 0 to 70°C., per mole of starting compound of the formula (I-1-a to I-5-a).

[0541] Process (I) is preferably carried out in the presence of adiluent.

[0542] Possible diluents are all inert polar organic solvents, such asethers, amides, ketones, carboxylic acid esters, nitriles, sulphones,sulphoxides or halogenated hydrocarbons such as methylene chloride.

[0543] Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide andmethylene chloride are preferably employed.

[0544] If, in a preferred embodiment, the enolate salt of the compounds(I-1-a) to (I-5-a) is prepared by addition of strong deprotonatingagents (e.g. sodium hydride or potassium tertiary butoxide), the furtheraddition of acid-binding agents can be dispensed with.

[0545] If acid-binding agents are employed, customary inorganic ororganic bases are suitable; those which may be mentioned by way ofexample are sodium hydroxide, sodium carbonate, potassium carbonate,pyridine and triethylamine.

[0546] The reaction can be carried out at atmospheric pressure or atelevated pressure, preferably it is carried out at atmospheric pressure.Work-up takes place according to customary methods

[0547] Process (J) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are each reacted withphosphorus compounds of the formula (XIV), if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.

[0548] In preparation process (J), to obtain compounds of the formulae(I-1-e) to (I-5-e), 1 to 2, preferably 1 to 1.3, mol of the phosphoruscompound of the formula (XIV) are reacted at temperatures between −40°C. and 150° C., preferably between −10 and 110° C., relative to 1 mol ofthe compounds (I-1-a) to (I-5-a).

[0549] Process (J) is preferably carried out in the presence of adiluent.

[0550] Possible diluents are all inert, polar organic solvents, such asethers, carboxylic acid esters, halogenated hydrocarbons, ketones,amides, nitriles, sulphones, sulphoxides etc.

[0551] Acetonitrile, dimethyl sulphoxide, tetrahydrofuran,dimethylformamide and methylene chloride are preferably employed.

[0552] Possible acid-binding agents optionally added are customaryinorganic or organic bases such as hydroxides, carbonates or amines.Those which may be mentioned by way of example are sodium hydroxide,sodium carbonate, potassium carbonate, pyridine and triethylamine.

[0553] The reaction can be carried out at atmospheric pressure or atelevated pressure, preferably at atmospheric pressure. Work-up takesplace according to customary methods of organic chemistry. The finalproducts are preferably purified by crystallization, chromatographicpurification or by so-called “incipient distillation”, i.e. removal ofthe volatile constituents in vacuo.

[0554] Process (K) is characterized in that compounds of the formulae(I-1-a) to (I-5-a) are each reacted with metal hydroxides or metalalkoxides of the formula (XV) or amines of the formula (XVI), ifappropriate in the presence of a diluent.

[0555] Diluents which can be employed in process (K) according to theinvention are preferably ethers such as tetrahydrofuran, dioxane,diethyl ether or else alcohols such as methanol, ethanol, isopropanol,but also water. Process (K) according to the invention is in generalcarried out under atmospheric pressure. The reaction temperature is in(general between −20° C. and 100° C., preferably between 0° C. and 50°C.

[0556] Process (L) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-5-a) are each reacted with (Lα)compounds of the formula (XVII), if appropriate in the presence of adiluent and if appropriate in the presence of a catalyst, or (Lβ) withcompounds of the formula (XVIII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent.

[0557] In preparation process (Lα), about 1 mol of isocyanate of theformula (XVII) is reacted at 0 to 100° C., preferably at 20 to 50° C.,per mole of starting compound of the formulae (I-1-a) to (I-5-a).

[0558] Process (Lα) is preferably carried out in the presence of adiluent.

[0559] Possible diluents are all inert organic solvents, such asaromatic hydrocarbons, halogenated hydrocarbons, ethers, amides,nitriles, sulphones or sulphoxides.

[0560] Catalysts can optionally be added to accelerate the reaction. Thecatalysts employed can very advantageously be organotin compounds, e.g.dibutyltin dilaurate.

[0561] The reaction is preferably carried out at atmospheric pressure.

[0562] In preparation process (Lβ), about 1 mol of carbamoyl chloride ofthe formula (XVIII) is reacted at 0 to 150° C., preferably at 20 to 70°C., per mole of starting compound of the formulae (I-1-a) to (I-5-a).

[0563] Possible diluents optionally added are all inert polar organicsolvents, such as ethers, carboxylic acid esters, nitriles, ketones,amides, sulphones, sulphoxides or halogenated hydrocarbons.

[0564] Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide ormethylene chloride are preferably employed.

[0565] If, in a preferred embodiment, the enolate salt of the compound(I-1-a) to (I-5-a) is prepared by addition of strong deprotonatingagents (e.g. sodium hydride or potassium tertiary butoxide), the furtheraddition of acid-binding agents can be dispensed with

[0566] If acid-binding agents are employed, customary inorganic ororganic bases are suitable; those which may be mentioned by way ofexample are sodium hydroxide, sodium carbonate, potassium carbonate,triethylamine or pyridine.

[0567] The reaction can be carried out at atmospheric pressure or atelevated pressure, preferably at atmospheric pressure. Work-up takesplace according to customary methods.

[0568] The active compounds are suitable for controlling animal pests,preferably arthropods and nematodes, in particular insects andarachnida, which are encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienefield. They are active against normally sensitive and resistant speciesand against all or some stages of development. The above-mentioned pestsinclude:

[0569] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0570] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0571] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spec.

[0572] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0573] From the order of the Thysanura, for example, Lepisma saccharina.

[0574] From the order of the Collembola, for example, Onychiurusarmatus.

[0575] From the order of the Orthoptera, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica, Achetadomesticus, Gryllotalpa spp., Locusta migratoria migratorioides,Melanoplus differentialis and Schistocerca gregaria.

[0576] From the order of the Dermaptera, for example, Forficulaauricularia.

[0577] From the order of the Isoptera, for example, Reticulitermes spp.

[0578] From the order of the Anoplura, for example, Phylloxeravastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp.and Linognathus spp.

[0579] From the order of the Mallophaga, for example, Trichodectes spp.and Damalinea spp.

[0580] From the order of the Thysanoptera, for example, Hercinothripsfemoralis and Thrips tabaci.

[0581] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0582] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzusspp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelisbilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae,Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii,Aspidiotus hederae, Pseudococcus spp. and Psylla spp.

[0583] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp. Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestrabrassicae, Panolis flammea, Prodenia litura, Spodoptera spp.,Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustanubilalis, Ephestia kuehniella, Galleria mellonella, Tineolabisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoeciapodana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella,Homona magnanima and Tortrix viridana.

[0584] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus,Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae,Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis,Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilusspp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchusassimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenusspp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor,Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallonsolstitialis and Costelytra zealandica.

[0585] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0586] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

[0587] From the order of the Siphonaptera, for example, Xenopsyllacheopis and Ceratophyllus spp

[0588] From the order of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

[0589] From the order of the Acarina, for example, Acarus siro, Argasspp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis,Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyommaspp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp.,Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. andTetranychus spp.

[0590] The active compounds according to the invention are distinguishedby a high insecticidal and acaricidal activity.

[0591] They can be used to particularly good effect for controllinginsects which are injurious to plants, such as, for example, against thelarvae of the mustard beetle (Phaedon cochleariae), against the larvaeof the green rice leaf hopper (Nephotettix cincticeps) or against thecaterpillars of the cabbage moth (Plutella maculipennis).

[0592] The active compounds according to the invention can furthermorebe used as defoliants, desiccants, agents for destroying broad-leavedplants and, especially, as weed-killers. By weeds, in the broadestsense, there are to be understood all plants which grow in locationswhere they are undesired. Whether the substances according to theinvention act as total or selective herbicides depends essentially onthe amount used.

[0593] The dosages of the active compounds according to the inventionnecessary for controlling weeds are betweeen 0.001 and 10 kg/ha,preferably between 0.005 and 5 kg/ha.

[0594] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0595] Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium,Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica,Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea,Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum,Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura,Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus andTaraxacum.

[0596] Dicotyledon crops of the genera: Gossypium, Glycine, Beta,Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

[0597] Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

[0598] Monocotyledon crops of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

[0599] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0600] The compounds are suitable, depending on the concentration, forthe total control of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for controlling weeds inperennial cultures, for example afforestations, decorative treeplantings, orchards, vineyards, citrus groves, nut orchards, bananaplantations, coffee plantations, tea plantations, rubber plantations,oil palm plantations, cocoa plantations, soft fruit plantings andhopfields, on lawns, turf and pasture-land, and for the selectivecontrol of weeds in annual cultures.

[0601] The active compounds according to the invention are very highlysuitable for the selective control of monocotyledon weeds in dicotyledoncrops pre- and post-emergence. They can be employed to very good effectfor the control of grass weeds, for example in cotton or sugar beet.

[0602] The active compounds can be converted into the customaryformulations, such as solutions, emulsions, wettable powders,suspensions, powders, dusting, agents, pastes, soluble powders,granules, suspension-emulsion concentrates, natural and syntheticmaterials impregnated with active compound, and very fine capsules inpolymeric substances.

[0603] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is liquid solventsand/or solid carriers, optionally with the use of surface-active agents,that is emulsifying agents and/or dispersing agents and/or foam-formingagents.

[0604] In the case of the use of water as an extender, organic solventscan, for example, also be used as auxiliary solvents. As liquidsolvents, there are suitable in the main: aromatics, such as xylene,toluene or alkylnaphthalenes, chlorinated aromatics and chlorinatedaliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes ormethylene chloride, aliphatic hydrocarbons, such as cyclohexane orparaffins, for example petroleum fractions, mineral and vegetable oils,alcohols, such as butanol or glycol as well as their ethers and esters,ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water.

[0605] As solid carriers there are suitable:

[0606] for example ammonium salts and ground natural minerals, such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates, as solid carriers for granulesthere are suitable: for example crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite, as well assynthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; as emulsifying and/or foam-forming agents there are suitable:for example non-ionic and anionic emulsifiers, such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,arylsulphonates as well as albumen hydrolysis products; as dispersingagents there are suitable: for example lignin-sulphite waste liquors andmethylcellulose.

[0607] Adhesives such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations Further additives can bemineral and vegetable oils.

[0608] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0609] The formulations in general contain between 0.1 and 95 percent byweight of active compound, preferably between 0.5 and 90%.

[0610] The active compound according to the invention can be present inits commercially available formulations and in the use forms preparedfrom these formulations, as a mixture with other active compounds, suchas insecticides, attractants, sterilizing agents, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas and substances produced bymicroorganisms.

[0611] Examples of particularly advantageous mixture components are thefollowing compounds:

[0612] Fungicides:

[0613] 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxy-phenyl)-acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoximino[ alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,

[0614] benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate,

[0615] calcium polysulphide, captafol, captan, carbendazim, carboxin,quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate,cufraneb, cymoxanil, cyproconazole, cyprofuram,

[0616] dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran,diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine,drazoxolon,

[0617] edifenphos, epoxyconazole, ethirimol, etridiazole,

[0618] fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil,fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, fluoromide, fluquinconazole,flusilazole, flusulfamide, flutolanil, flutriafol, folpet,fosetyl-aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox,

[0619] guazatine,

[0620] hexachlorobenzene, hexaconazole, hymexazol,

[0621] imazalil, imibenconazole, iminoctadine, iprobenfos (IBP),iprodione, isoprothiolane,

[0622] kasugamycin, copper preparations such as: copper hydroxide,copper naphthenate, copper oxychloride, copper sulphate, copper oxide,oxine-copper and Bordeaux mixture, mancopper, mancozeb, maneb,mepanipyrim, mepronil, metalaxyl, metconazole, methasulfocarb,methfuroxam, metiram, metsulfovax, myclobutanil,

[0623] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0624] ofurace, oxadixyl, oxamocarb, oxycarboxin,

[0625] pefurazoate, penconazole, pencycuron, phosdiphen, phthalide,pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz,procymidone, propamocarb, propiconazole, propineb, pyrazophos,pyrifenox, pyrimethanil, pyroquilon,

[0626] quintozene (PCNB),

[0627] sulfur and sulfur preparations,

[0628] tebuconazole, tecloftalam, tecnazene, tetraconazole,thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide,tricyclazole, tridemorph, triflumizole, triforine, triticonazole,

[0629] validamycin A, vinclozolin,

[0630] zineb, ziram

[0631] Bactericides:

[0632] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0633] Insecticides/Acaricides/Nematicides:

[0634] abamectin, abamectin, AC 303 630, acephate, acrinathrin,alanycarb, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541,azadirachtin, azinphos A, azinphos M, azocyclotin,

[0635]Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap,beta-cyfluthrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb,buprofezin, butocarboxim, butylpyridaben,

[0636] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos,chlorfenvinphos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifosM, cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

[0637] deltamethrin, demeton-M, demeton-S, demeton-S-methyl,diafenthiuron, diazinon, dichlofenthion, dichlorvos, dicliphos,dicrotophos, diethion, diflubenzuron, dimethoate, dimethylvinphos,dioxathion, disulfoton,

[0638] edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion,ethofenprox, ethoprophos, etrimphos,

[0639] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad,fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam,flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate,fonophos, formothion, fosthiazate, fubfenprox, furathiocarb,

[0640] HCH, heptenophos, hexaflumuron, hexythiazox,

[0641] imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb,isoxathion, ivermectin,

[0642] lambda-cyhalothrin, lufenuron,

[0643] malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde,methacrifos, methamidophos, methidathion, methiocarb, methomyl,metolcarb, milbemectin, monocrotophos, moxidectin,

[0644] naled, NC 184, NI 25, nitenpyram,

[0645] omethoate, oxamyl, oxydemethon M, oxydeprofos,

[0646] parathion A, parathion M, permethrin, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M,pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos,prothoate, pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin,pyrethrum, pyridaben, pyrimidifen, pyriproxifen,

[0647] quinalphos,

[0648] RH 5992,

[0649] salithion, sebufos, silafluofen, sulfotep, sulprofos,

[0650] tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron,tefluthrin, temephos, terbam, terbufos, tetrachlorvinphos, thiafenox,thiodicarb, thiofanox, thiomethon, thionazin, thuringiensin,tralomethrin, triarathen, triazophos, triazuron, trichlorfon,triflumuron, trimethacarb,

[0651] vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.

[0652] Herbicides:

[0653] for example anilides such as, for example, diflufenican andpropanil; arylcarboxylic acids such as, for example, dichloropicolinicacid, dicamba and picloram; aryloxyalkanoic acids such as, for example,2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr;aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl,fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl andquizalofop-ethyl; azinones such as, for example, chloridazon andnorflurazon; carbamates such as, for example, chlorpropham, desmedipham,phenmedipham and propham; chloroacetanilides such as, for example,alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlorand propachlor; dinitroanilines such as, for example, oryzalin,pendimethalin and trifluralin; diphenyl ethers such as, for example,acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen andoxyfluorfen, ureas such as, for example, chlortoluron, diuron,fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylaminessuch as, for example, alloxydim, clethodim, cycloxydim, sethoxydim andtralkoxydim; imidazolinones such as, for example, imazethapyr,imazamethabenz, imazapyr and imazaquin; nitriles such as, for example,bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example,mefenacet; sulfonylureas such as, for example, amidosulfuron,bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron,metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl,thifensulfuron-methyl, triasulfuron and tribenuron-methyl;thiocarbamates such as, for example, butylate, cycloate, di-allate,EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate;triazines such as, for example, atrazine, cyanazine, simazine, simetryn,terbutryn and terbutylazine; triazinones such as, for example,hexazinone, metamitron and metribuzin; others such as, for example,aminotriazole, benfuresate, bentazone, cinmethylin, clomazone,clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone,glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac,sulphosate and tridiphane.

[0654] The active compound according to the invention can furthermore bepresent in its commercially available formulations and in the use formsprepared from these formulations, as a mixture with synergistic agents.Synergistic agents are compounds which increase the action of the activecompounds, without it being necessary for the synergistic agent added tobe active itself.

[0655] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[0656] The compounds are employed in a customary manner appropriate forthe use forms

[0657] When used against hygiene pests and pests of stored products, theactive compounds are distinguished by an excellent residual action onwood and clay as well as a good stability to alkali on limed substrates.

[0658] The active compounds according to the invention are not onlyactive against plant, hygiene and stored-product pests, but also, in theveterinary medicine sector, against animal parasites (ectoparasites),such as ixodid ticks, argasid ticks, scab mites, trombiculid mites,flies (stinging and sucking), parasitic fly larvae, lice, hair lice,bird lice and fleas. These parasites include:

[0659] From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

[0660] From the order of the Mallophagida and the sub-orders Amblycerinaand Isochnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

[0661] From the order of the Diptera and the sub-orders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[0662] From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

[0663] From the order of the Heteropterida, for example, Cimex spp.,Triatoma spp., Rhodnius spp. and Panstrongylus spp.

[0664] From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica and Supella spp.

[0665] From the sub-class of the Acaria (Acarida) and the orders of theMeta- and Mesostigmata, for example Argas spp., Ornithodorus spp.,Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp, Dermacentorspp., Haemaphysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroaspp.

[0666] From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp, Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0667] For example, they show an outstanding activity against Boophilusmicroplus and Lucilia cuprina.

[0668] The active compounds of the formula (I) according to theinvention are also suitable for combating arthropods which attackagricultural livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese, honey bees, other domestic animals, such as, for example,dogs, cats, cage birds, aquarium fish, and so-called experimentalanimals, such as, for example, hamsters, guinea-pigs, rats and mice. Bycombating these arthropods, it is intended to reduce mortality anddecreased performance (in meat, milk, wool, hides, eggs, honey and thelike), so that more economical and simpler animal keeping is madepossible by using the active compounds according to the invention.

[0669] In the veterinary sector, the active compounds according to theinvention are used in a known manner by enteral administration, forexample in the form of tablets, capsules, drinks, drenches, granules,pastes, boluses, the feed-through method, suppositories, by parenteraladministration, such as, for example, by means of injections(intramolecular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal application, by dermal administration, forexample in the form of dipping or bathing, spraying, pouring-on andspotting-on, washing, dusting, and with the aid of shaped articles whichcomprise active compound, such as collars, ear tags, tail marks, limbbands, halters, marking devices and the like.

[0670] When administered to livestock, poultry, domestic animals and thelike, the active compounds of the formula (I) can be used asformulations (for example powders, emulsions, flowables) which comprisethe active compounds in an amount of 1 to 80% by weight, either directlyor after dilution by a factor of 100 to 10,000, or they may be used inthe form of a chemical bath.

[0671] Furthermore, it has been found that the compounds of the formula(I) according to the invention have a potent insecticidal action againstinsects which destroy industrial materials.

[0672] The following insects may be mentioned by way of example and asbeing preferred, but without any limitation:

[0673] Beetles, such as

[0674]Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,Xestobium rufovillosum, Pulinus pecticornis, Dendrobium pertinex,Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus,Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

[0675] Dermapterans, such as

[0676]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerusaugur.

[0677] Termites, scuh as

[0678]Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Recticulitermes flavipes, Reticulitermes santonensis,Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsisnevdensis, Coptotermes formosanus.

[0679] Bristletails, such as

[0680]Lepisma saccharina.

[0681] Industrial materials are to be understood as meaning, in thepresent context, non-live materials, such as, preferably, syntheticmaterials, glues, sizes, paper and board, leather, wood and timberproducts, and paint.

[0682] The materials to be very particularly protected against attack byinsects are wood and timber products.

[0683] Wood and timber products which can be protected by thecomposition according to the invention or mixtures comprising such acomposition are to be understood as meaning, for example, constructiontimber, wooden beams, railway sleepers, bridge components, jetties,wooden vehicles, boxes, pallets, containers, telephone poles, woodlagging, windows and doors made of wood, plywood, particle board,joiner's articles, or wood products which, quite generally, are used inthe construction of houses or in joinery.

[0684] The active compounds can be used as such, in the form ofconcentrates or generally customary formulations, such as powders,granules, solutions, suspensions, emulsions or pastes.

[0685] The formulations mentioned can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if appropriate desiccants and UV stabilizers and, ifappropriate, colorants and pigments and other processing auxiliaries.

[0686] The insecticidal compositions or concentrates used for theprotection of wood and wooden materials comprise the active compoundaccording to the invention at a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

[0687] The amount of the compositions or concentrates employed dependson the species and the occurrence of the insects and on the medium. Theoptimum rate of application can be determined upon use in each case bytest series. However, in general, it suffices to employ 0.0001 to 20% byweight, preferably 0.001 to 10% by weight, of the active compound, basedon the material to be protected.

[0688] The solvent and/or diluent used is an organochemical solvent orsolvent mixture and/or an oily or oil-type organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water and, if appropriate, an emulsifierand/or wetting agent.

[0689] Organochemical solvents which are preferably employed are oily oroil-type solvents having an evaporation number of above 35 and aflashpoint of above 30° C., preferably above 45° C. Substances which areused as such oily and oil-type solvents which have low volatility andare insoluble in water are suitable mineral oils or their aromaticfractions, or mineral-oil-containing solvent mixtures, preferably whitespirit, petroleum and/or alkylbenzene.

[0690] Substances which are advantageously used are mineral oils with aboiling range of 170 to 220° C., white spirit with a boiling range of170 to 220° C., spindle oil with a boiling range of 250 to 350° C.,petroleum or aromatics of boiling range 160 to 280° C., essence ofterpentine and the like.

[0691] In a preferred embodiment, liquid aliphatic hydrocarbons with aboiling range of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

[0692] The organic oily or oil-type solvents of low volatility having anevaporation number of above 35 and a flashpoint of above 30° C.,preferably above 45° C., can be partially replaced by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flashpoint ofabove 30° C., preferably above 45° C., and that the insectide/fungicidemixture is soluble or emulsifiable in this solvent mixture.

[0693] In a preferred embodiment, part of the organochemical solvent orsolvent mixture is replaced by an aliphatic polar organochemical solventor solvent mixture. Substances which are preferably used are aliphaticorganochemical solvents having hydroxyl and/or ester and/or ethergroups, such as, for example, glycol ether, esters and the like.

[0694] The organochemical binders used within the scope of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se and can be diluted with water and/or are soluble ordispersible or emulsifiable in the organochemical solvents employed, inparticular binders composed of, or comprising, an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenol resin, hydrocarbon resin, such asindene/coumarone resin, silicone resin, drying vegetable and/or dryingoils and/or physically drying binders based on a natural and/orsynthetic resin.

[0695] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Up to 10% of bitumen orbituminous substances can also be used as binders. In addition,colorants, pigments, water repellents, odour-masking substances andinhibitors or anticorrosives known per se and the like can also beemployed.

[0696] The composition or the concentrate preferably comprises, inaccordance with the invention, at least one alkyd resin or modifiedalkyd resin and/or a drying vegetable oil as the organochemical binder.Preferably used according to the invention are alkyd resins with an oilcontent of over 45% by weight, preferably 50 to 68% by weight.

[0697] All or some of the abovementioned binder can be replaced by afixative (mixture) or a plasticizer (mixture). These additives areintended to prevent volatilization of the active compounds andcrystallization or precipitation. They preferably replace 0.01 to 30% ofthe binder (based on 100% of binder employed).

[0698] The plasticizers are from the chemical classes of the phthalicesters, such as dibutyl phthalate, dioctyl phthalate or benzylbutylphthalate, the phosphoric esters, such as tributyl phosphate, the adipicesters, such as di-(2-ethylhexyl) adipate, the stearates, such as butylstearate or amyl stearate, the oleates, such as butyl oleate, theglycerol ethers or relatively high-molecular-weight glycol ethers,glycerol esters and p-toluene-sulphonic esters.

[0699] Fixatives are chemically based on polyvinyl alkyl ethers, suchas, for example, polyvinyl methyl ether, or ketones, such asbenzophenone or ethylenebenzophenone.

[0700] Particularly suitable as a solvent or diluent is also water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

[0701] Particularly effective protection of wood is achieved bylarge-scale industrial impregnation processes, for example vacuum,double-vacuum or pressure processes.

[0702] If appropriate, the ready-to-use compositions can additionallycomprise other insecticides and, if appropriate, additionally one ormore fungicides.

[0703] Suitable additional components which may be admixed are,preferably, the insecticides and fungicides mentioned in WO 94/29 268.The compounds mentioned in that document are expressly part of thepresent application.

[0704] Very particularly preferred components which may be admixed areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron and triflumuron, and fungicides, such asepoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole,cyproconazole, metconazole, imazalil, dichlofluanid, tolylfluanid,3-iodo-2-propinylbutyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

[0705] The preparation and the use of the active compounds according tothe invention can be seen from the examples which follow.

PREPARATION EXAMPLES Example (I-1-a-1)

[0706]

[0707] Under reflux, 29.6 g (0.0764 mol) of the compound prepared by themethod of Example (II-1) in 160 ml of anhydrous toluene are addeddropwise to 22.7 g (0.2 mol) of potassium tert-butoxide in 60 ml ofanhydrous tetrahydrofuran (THF), and the mixture is stirred under refluxfor 1.5 hours. For work-up, 230 ml of water are added, the aqueous phaseis separated off, the toluene phase is extracted with 110 ml of water,and the aqueous phases are combined, washed with toluene and acidifiedat 10 to 20° C. with conc. HCl to pH 1. The product is filtered offunder suction, washed, dried and washed by stirring in methyl tert-butylether (MTB) ether/n-hexane.

[0708] Yield: 13.7 g (56% of theory), mp.: >220° C.

[0709] The compounds of the formula (I-1-a) given below were preparedanalogously or in accordance with the general preparation instructions:TABLE 57 (I-1-a)

Ex. No. V W X Y Z A B mp. ° C. Isomer I-1-a-2 H CH₃ CH₃ H Cl—(CH₂)₂—CHOCH₃—(CH₂)₂— 219 β I-1-a-3 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— 122 β I-1-a-4 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-5 H CH₃ CH₃ CH₃ Br—(CH₂)₂—CHCH₃—(CH₂)₂—   169 β I-1-a-6 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—O—(CH₂)₂— >220 — I-1-a-7 H CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ >220 —I-1-a-8 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₂—CHOC₂H₅—(CH₂)₂—   225 β I-1-a-9 H CH₃CH₃ CH₃ CH₃ i-C₃H₇ CH₃   185 — I-1-a-10 H CH₃ CH₃ CH₃ Br—(CH₂)₂—CHOCH₃—(CH₂)₂—   180 β I-1-a-11 CH₃ CH₃ CH₃ H CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— >220 β I-1-a-12 CH₃ CH₃ CH₃ H CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-13 CH₃ CH₃ H CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— >220 β I-1-a-14 CH₃ CH₃ H CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-15 H CH₃ CH₃ H CH₃—(CH₂)₂—O—(CH₂)₂— >220 — I-1-a-16 H CH₃ CH₃ H Br—(CH₂)₂—CHCH₃—(CH₂)₂— >220 β I-1-a-17 H CH₃ CH₃ H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-18 H Cl Cl H Br—(CH₂)₂—CHCH₃—(CH₂)₂— >220 β I-1-a-19 H Cl Cl H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-20 H Br Br —(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— >220 β I-1-a-21 H Br Br —(CH₂)₃——(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-22 H CH₃ OCH₃ H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-23 H CH₃ OCH₃ H Br—(CH₂)₂—CHCH₃—(CH₂)₂— >220 β I-1-a-24 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₅—   143 —I-1-a-25 H Cl Cl Cl CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-26 CH₃ CH₃CH₃ CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— >220 β I-1-a-27 H CH₃ CH₃ CH₃ CH₃—(CH₂)₄— >225 I-1-a-28 H CH₃ H H CH₃ —(CH₂)—CHOCH₃—(CH₂)₂— >220 I-1-a-29CH₃ CH₃ CH₃ CH₃ CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— >220 I-1-a-30 H Cl Cl Cl CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— >220 I-1-a-31 H Br Br Br CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— >220 I-1-a-32 H Br Br Br CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— >220

Example (I-1-b-1)

[0710]

[0711] 384 g (0.012 mol) of the compound prepared by the method ofExample (I-1-a-1) and 2.5 ml (18 mmol) of triethylamine in 70 ml ofanhydrous methylene chloride are treated with 2.2 ml (0.18 mol) ofisovaleryl chloride in 5 ml of anhydrous methylene chloride at 0 to 10°C., and the mixture is stirred at room temperature until the reactionhas ended (TLC check). For work-up, the mixture is washed twice with 50ml of 0.5 N aqueous sodium hydroxide solution, dried over magnesiumsulphate and evaporated. The crude product is recrystallized from MTBether/n-hexane.

[0712] Yield. 1.6 g (33% of theory), mp.: 218° C.

[0713] The compounds of the formula (I-b-1) given below are obtainedanalogously or in accordance with the general preparation instructions:TABLE 58 (I-1-b)

Ex No. V W X Y Z A B R¹ mp ° C. Isomer I-1-b-2 H CH₃ CH₃ H Cl—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇ 211 β I-1-b-3 H CH₃ CH₃ H Cl—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 215 β I-1-b-4 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇ 217 β I-1-b-5 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₄H₉ >220 β I-1-b-6 H CH₃ CH₃ CH₃ Br—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 205 β I-1-b-7 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 194 β I-1-b-8 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— t-C₄H₉— 186 β CH₂ I-1-b-9 H CH₃ CH₃ CH₃ Br—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 211 β I-1-b-10 H CH₃ CH₃ H Br—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇ 205 β I-1-b-11 H Br Br —(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇ >220 β I-1-b-12 H CH₃ OCH₃ H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 205 β I-1-b-13 CH₃ CH₃ H CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 198 β I-1-b-14 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 172 β I-1-b-15 H CH₃ CH₃ CH₃ CH₃ CH₃i-C₃H₇ i-C₃H₇ 142 I-1-b-16 H CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ i-C₃H₇ 147 I-1-b-17H Cl Cl H Br —(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ >220 β I-1-b-18 H CH₃ H H CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 189 β I-1-b-19 H Br Br —(CH₂)₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 212 β I-1-b-20 CH₃ CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 205 β I-1-b-21 H Cl Cl Cl CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 188 β I-1-b-22 H Cl Cl Cl CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇ 204 β I-1-b-23 H Br Br Br CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— i-C₃H₇ 226 β I-1-b-24 H Br Br Br CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 188 β

Example (I-1-c-1)

[0714]

[0715] At 0 to 10° C., 1.2 ml (0.012 mol) of ethyl chloroformate in 5 mlof anhydrous methylene chloride are added dropwise to 3.84 g (0.012 mol)of the compound prepared by the method of Example (I-1-a-1) and 1.7 ml(0.012 mol) of triethylamine in 70 ml of anhydrous CH₂Cl₂, and themixture is stirred at room temperature until the reaction has ended (TLCcheck). For work-up, the mixture is washed twice with 50 ml of 0.5 Naqueous sodium hydroxide solution, dried over magnesium sulphate andevaporated.

[0716] Yield 3.6 g (76% of theory), mp.: >220° C.

[0717] The compounds of the formula (I-1-c) given below are obtainedanalogously or in accordance with the general preparation instructions:TABLE 59 (I-1-c)

Ex. No. V W X Y Z A B M R² mp. ° C. Isomer I-1-c-2 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— ∘ i-C₄H₉ 177 β I-1-c-3 H CH₃ CH₃ H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— ∘ C₂H₅ >220   β I-1-c-4 H CH₃ OCH₃ H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— ∘ C₂H₅ 207 β I-1-c-5 H CH₃ CH₃ CH₃ Br—(CH₂)₂—CHOCH₃—(CH₂)₂— ∘ C₂H₅ 214 β I-1-c-6 H Cl Cl H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— ∘ C₂H₅ >220   β I-1-c-7 H CH₃ CH₃ CH₃ CH₃ CH₃ CH₃∘ C₂H₅ 118 I-1-c-8 CH₃ CH₃ H CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— ∘ C₂H₅ 210 βI-1-c-9 H CH₃ H H CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— ∘ C₂H₅ 154 β I-1-c-10 H ClCl Cl CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— ∘ C₂H₅ 183 β I-1-c-11 H Cl Cl Cl CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— ∘ C₂H₅ 181 β I-1-c-12 H Br Br Br CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— ∘ C₂H₅ 188 β

Example (II-1)

[0718]

[0719] At 30 to 40° C., 16.7 g (0.0544 mol) of the compound prepared bythe method of Example (XXIX-1) in 160 ml of anhydrous methylene chlorideare added dropwise to 26.6 g (0.257 mol) of conc. sulphuric acid, andthe mixture is stirred for 2 hours at this temperature. 37 ml ofabsolute methanol are then added in such a way that the internaltemperature is about 40° C., and stirring is continued at 40 to 70° C.for a further 6 hours.

[0720] For work-up, the mixture is poured on 0.28 kg of ice, extractedwith methylene chloride, washed with aqueous sodium bicarbonatesolution, dried and evaporated. The residue is recrystallized frommethyl tert-butyl ether/n-hexane.

[0721] Yield: 16.5 g (89% of theory), mp.: 168° C.

Example (II-2)

[0722]

[0723] 15.9 g (0.08 mol) of 3-chloro-2,6-dimethylphenylacetic acid and17.7 ml (0.24 mol) of thionyl chloride are stirred for 30 minutes atroom temperature and subsequently at 80° C. until the evolution of gashas ceased. Excess thionyl chloride is removed at 50° C. under reducedpressure. 50 ml of anhydrous toluene are then added, and the solution isevaporated once again. The residue is taken up in 100 ml of anhydrousTHF (solution 1).

[0724] At 0 to 10° C., solution 1 is added dropwise to 16.8 g of methylcis-4-methylcyclohexylamine-1-carboxylate and 24.6 ml (0.176 mol) oftriethylamine in 160 ml of anhydrous THF, and the solution issubsequently stirred at room temperature for 1 hour. The mixture isfiltered under suction, washed with anhydrous THE and evaporated. Theresidue is taken up in methylene chloride, washed with 0.5 N HCl, driedand evaporated. The crude product is recrystallized from methyltert-butyl ether/n-hexane.

[0725] Yield: 26.9 g (74% of theory), mp.: 163° C.

[0726] The compounds of the formula (II) given below are preparedanalogously to Examples (II-1) and (II-2) and in accordance with thegeneral preparation instructions. TABLE 60 Compounds of the formula (II)

Ex No. V W X Y Z A B R⁸ mp. ° C. Isomer II-3 H CH₃ CH₃ H Cl−(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 154 β II-4 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 169 β Il-5 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 174 β II-6 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—O—(CH₂)₂— CH₃ 174 — II-7 H CH₃ CH₃ CH₃ Br —(CH₂)₂—CHCH₃—(CH₂)₂—CH₃ 166 β II-8 H CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ CH₃ 152 — II-9 H CH₃ CH₃ CH₃CH₃ —(CH₂)₂—CHOC₂H₅—(CH₂)₂— CH₃ 145 β II-10 H CH₃ CH₃ CH₃ CH₃ i-C₃H₇ CH₃CH₃  98 — II-11 H CH₃ CH₃ CH₃ Br —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 156 β II-12CH₃ CH₃ CH₃ H CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 181 β II-13 CH₃ CH₃ CH₃ HCH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 145 β II-14 CH₃ CH₃ H CH₃ CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— CH 161 β Il-15 CH₃ CH₃ H CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 166 β II-16 H CH₃ CH₃ H Br—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 154 β II-17 H CH₃ CH₃ H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 135 β II-18 H Cl Cl H Br—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 171 β II-19 H Cl Cl H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 160 β II-20 H Br Br —(CH₂)₃——(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 154 β II-21 H Br Br —(CH₂)₃₋—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 158 β II-22 H CH₃ OCH₃ H Br—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 174 β II-23 H CH₃ OCH₃ H Br—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 169 β II-24 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₅— CH₃136 — II-25 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₄— CH₃ 145 — II-26 CH₃ CH₃ CH₃ CH₃CH₃ —(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 182 β II-27 CH₃ CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 175 β II-28 H Cl Cl Cl CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 174 β II-29 H Cl Cl Cl CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 167 β II-30 H Br Br Br CH₃—(CH₂)₂—CHCH₃—(CH₂)₂— CH₃ 210 β II-31 H Br Br Br CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— CH₃ 169 β

Example (XXIX-1)

[0727]

[0728] Starting from 12.6 g of 3-chloro-2,6-dimethylphenylacetic acid,solution 1 is prepared as described in Example (II-2).

[0729] At 0 to 10° C., solution 1 is added dropwise to 15.1 g of4-amino-4-cyano-tetrahydropyran (70% strength) and 9.2 ml (0.066 mol) oftriethylamine in 120 ml of anhydrous THE, and the mixture is stirred fora further hour at room temperature. The mixture is then evaporated andthe residue is taken up in methylene chloride, washed with 0.5 N HCl,dried and evaporated. The crude product is recrystallized from MTBether/n-hexane.

[0730] Yield. 16.7 g (90% of theory), mp.: 176° C.

[0731] The compounds of the formula (XXIX) given below are preparedanalogously to Example (XXIX-1) and in accordance with the generalpreparation instructions: TABLE 61 (XXIX)

Ex No. V W X Y Z A B mp. ° C. XXIX-2 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₂—O—(CH₂)₂—163 XXIX-3 H CH₃ CH₃ CH₃ CH₃ i-Pr CH₃ 162 XXIX-4 H CH₃ CH₃ CH₃ CH₃-(CH2)4- 185

Example (I-2-a-1)

[0732]

[0733] 8.42 g (75 mmol) of potassium tert-butoxide are initially chargedin 50 ml of anhydrous tetrahydrofuran (THF), and at 0 to 10° C. asolution of 17.62 g (50 mmol) of 1-ethyloxycarbonyl-cyclohexyl3-chloro-2,6-dimethylphenylacetate prepared by the method of Example(III-1) in 50 ml of anhydrous THF is added dropwise, and the solution isstirred at room temperature overnight.

[0734] For work-up, the reaction mixture is poured into 600 ml of water,acidified with 10% strength hydrochloric acid, the product is thenfiltered off with suction, taken up in methylene chloride, concentrated,and the crystals are triturated with petroleum ether.

[0735] Yield. 9.7 g (63% of theory) of mp.: 193° C.

[0736] The compounds (I-2-a) given below are obtained analogous toExample (I-2-a-1) and in accordance with the general preparationinstructions: TABLE 62 Compounds of the formula (I-2-a)

Ex. No. V W X Y Z A B mp. ° C. I-2-a-2 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₅—204-205 I-2-a-3 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— 113-118 I-2-a-4CH₃ CH₃ CH₃ H CH₃ —(CH₂)₅— >250 I-2-a-5 CH₃ CH₃ CH₃ H CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— 115-118

Example (I-2-b-1)

[0737]

[0738] 3.06 g (10 mmol) of the compound prepared by the method ofExample I-2-a-1 are initially charged in 40 ml of anhydrous THF, 1.1 g(11 mmol) of triethylamine are added, a solution of 1.2 g (10 mmol) ofpivaloyl chloride is added dropwise while cooling with ice, and stirringat room temperature is continued overnight. For work-up, the solution isconcentrated, stirred with water, filtered off with suction, dried, theresidue is taken up in ether, washed with 1 N NaOH, and the organicphase is dried over MgSO₄ and evaporated. For further purification, thecrude product is mixed with a little petroleum ether.

[0739] Yield 3.1 g (79% of theory) of mp.: 126° C.

[0740] The compounds of the formula (I-2-b) given below are obtainedanalogously or in accordance with the general preparation instructions.TABLE 63 Compounds of the formula (I-2-b) (I-2-b)

Ex. No. V W X Y Z A B R¹ mp. ° C. I-2-b-2 H CH₃ CH₃ H Cl —(CH₂)₅—t-C₄H₉—CH₂— 125 I-2-b-3 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₅— t-C₄H₉— 117-119I-2-b-4 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— t-C₄H₉— 150-153 I-2-b-5CH₃ CH₃ CH₃ H CH₃ —(CH₂)₅— t-C₄H₉— 143-145 I-2-b-6 CH₃ CH₃ CH₃ H CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— t-C₄H₉— 177-179 I-2-b-7 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— i-C₃H₇ 148

Example I-2-c-1

[0741]

[0742] 0.68 g (5 mmol) of isobutyl chloroformate are added dropwise to1.50 g (5 mmol) of the compound prepared by the method of Example(I-2-a-4) and 0.55 g (5.5 mmol) of triethylamine in 20 ml ofdichloromethane at room temperature. Stirring is continued for 2 hours.The mixture is then washed with 10% strength aqueous citric acid and 1 Naqueous sodium hydroxide solution, and the dichloromethane phase isdried and concentrated. The residue, which is obtained as an oil, isstirred with petroleum ether, and the solid which forms is filtered offwith suction.

[0743] Yield 0.76 g, mp.: 118 to 119° C.

[0744] The compounds of the formula (I-2-c) given below are obtainedanalogously or in accordance with the general preparation instructions.TABLE 63a (I-2-c)

Ex. No. V W X Y Z A B M R² mp. ° C. Isomer I-2-c-2 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— O CH₂-i-C₃H₇ 1) β I-12c-3 H CH₃ CH₃ CH₃ CH₃—(CH₂)₂—CHOCH₃—(CH₂)₂— S i-C₃H₇ 2) β

Example (III-1)

[0745]

[0746] 10.85 g (50 mmol) of 3-chloro-2,6-dimethyl-phenylacetyl chloridetogether with 8.6 g (50 mmol) of ethyl 1-hydroxy-cyclohexanecarboxylateare boiled for 1 h in 100 ml of toluene, and the solution is thenevaporated.

[0747] Yield. 17.5 g (quantitative) of 1-ethoxycarbonyl-cyclohexyl3-chloro-2,6-dimethyl-phenylacetate as a colourless oil.

[0748] GC/MS m/e⁻=M⁺ 352 (6%), 155 (100%), 109 (48%), 81 (76%), 29 (76%)TABLE 64 Compounds of the formula (III) (III)

Ex. No. V W X Y Z A B R⁸ III-2 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₅— C₂H₅ III-3 HCH₃ CH₃ CH₃ CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— C₂H₅ III-4 CH₃ CH₃ CH₃ H CH₃—(CH₂)₅— C₂H₅ III-5 CH₃ CH₃ CH₃ H CH₃ —(CH₂)₂—CHOCH₃—(CH₂)₂— C₂H₅

[0749] The compounds of the formula III are obtained as viscous oils andare in most cases without further purification and characterizationconverted into the compounds of the formula I-2-a.

Example (I-3-a-1)

[0750]

[0751] 16.2 g (35 mmol) of the compounds prepared by the method ofExample (IV-1) are initially charged in 70 ml of toluene and 35 ml oftrifluoroacetic acid and heated under reflux for 5 hours. Thetrifluoroacetic acid is evaporated under reduced pressure and theresidue is treated twice with toluene which is also evaporated underreduced pressure. The residue is taken up in 400 ml of water and 120 mlof methyl tert-butyl ether (MTB) ether, made alkaline using NaOH,extracted twice with MTB ether, and the aqueous phase is acidified withhydrochloric acid. The aqueous phase is extracted 3 times with MTBether, the organic phases are dried and concentrated.

[0752] Yield: 8.5 g (78% of theory); mp.: 226-231° C.

Example (I-3-b-1)

[0753]

[0754] 1.5 g (4.7 mmol) of the compound prepared by the method ofExample (I-3-a-1) in 20 ml of absolute methylene chloride are treatedwith 0.98 ml (1.5 eq) of triethylamine. While cooling with ice, 0.86 g(1.5 eq) of ethoxyacetyl chloride dissolved in 3 ml of absolutemethylene chloride are added dropwise. The solution is stirred for oneto two hours at room temperature and washed twice with 10% strengthcitric acid, and the combined aqueous, acidic phases are extracted withmethylene chloride. The combined organic phases are washed 2 times with1 N NaOH, and the aqueous alkaline phases are subsequently extractedwith methylene chloride. The combined organic phases are dried andconcentrated.

[0755] Yield: 1.70 g (86% of theory), oil.

[0756]¹H-NMR (400 MHz, CDCl₃): 1.08 (t, 3H, 1.1-2.1 (m, 10H); 2.1-2.2(4s, 12H); 3.1 (q, 2H); 3.9 (m, 2H); 6.83 (s, 1H).

Example (I-3-b-2)

[0757] Analogously to Example (I-3-b-1), the compound below, which isobtained as an oil, was prepared by using pivaloyl chloride.

[0758] Yield: 2.00 g (100% of theory).

Example (I-3-c-1)

[0759]

[0760] The reaction of 1.5 g (4.7 mmol) of the compound prepared by themethod of Example (I-3-a-1) with 0.91 ml (1.5 eq) of isobutylchloroformate under the reaction conditions described in Example(I-3-b-1) affords 1.85 g (94% of theory) of the compound shown above.

[0761] mp.: 83-89° C.

Example (IV-1)

[0762]

[0763] 1 drop of dimethylformamide (DMF) and then 11.4 g (96 mmol) ofthionyl chloride are added to 18 g (64 mmol) of the compound

[0764] in 70 ml of absolute toluene. The solution is stirred for 5minutes at room temperature and subsequently at 100° C. until the gasformation has ended. The mixture is concentrated under reduced pressure,treated twice with toluene which is distilled off again in each case,and the mixture is subsequently stirred for 1 hour under high vacuum.The acid chloride obtained is dissolved in 40 ml of absolutetetrahydrofuran (THF) (solution A).

[0765] At about 0° C., 57 ml (177 mmol) of a solution of lithiumdiisopropylamide (LDA) in [lacuna] are initially charged in 100 ml ofabsolute THF. At this temperature, 22.1 g (107 mmol) of methyl2,3,4,6-tetramethylphenylacetate dissolved in 40 ml is of absolute THFare added dropwise, and stirring is continued for a further 30 minutes

[0766] Subsequently, again at about 0° C., solution A is added dropwiseand the mixture is stirred for 1 hour without cooling.

[0767] The mixture is admixed with 350 ml of MTB ether and a few dropsof water, washed twice with 10% strength aqueous ammonium chloridesolution, and the organic phase is dried and concentrated. The crudeproduct is stirred with petroleum ether. The product is filtered offwith suction and dried.

[0768] Yield: 16.20 g (54% of theory). mp.: 114-116° C.

Example (I-4-a-1)

[0769]

[0770] 2.4 g (10 mmol) of 2,3,5,6-tetramethyl-phenyl-chlorocarbonylketene are initially charged in 20 ml of toluene (p.a.). At roomtemperature, 1.35 g (10 mmol) of 2-pyridyl ethyl ketone are added, andthe solution is stirred under reflux for 8 hours. On cooling, theproduct crystallizes out. The precipitate is filtered off under suctionand washed twice with cyclohexane.

[0771] Yield: 1.4 g (41% of theory). mp.: 202-205° C.

[0772] The compounds of the formula (I-4-a) given in the table belowwere prepared analogously to Example (I-4-a-1) or according to thegeneral preparation instructions: TABLE 65 (I-4-a)

Ex. No. V W X Y Z A D mp. ° C. I-4-a-2 CH₃ CH₃ CH₃ H CH₃ CH₃ 4-F—C₆H₄204-206 I-4-a-3 CH₃ CH₃ CH₃ H CH₃ CH₃ t-C₄H₉ 222-224 I-4-a-4 H CH₃ CH₃CH₃ CH₃ CH₃ 4-F—C₆H₄ 236-238 I-4-a-5 H CH₃ CH₃ CH₃ CH₃ CH₃ Cyclo-pentylOil I-4-a-6 H CH₃ CH₃ CH₃ CH₃ CH₃ 2-Pyridyl 101-103 I-4-a-7 H CH₃ CH₃CH₃ CH₃ CH₃ 4-Pyridyl 300-302 I-4-a-8 H CH₃ CH₃ CH₃ CH₃ —(CH₂)₄— 165-168I-4-a-9 H CH₃ CH₃ CH₃ CH₃ —C(CH₃)₂OC(CH₃)₂— 178-180

Example I-4-b-1

[0773]

[0774] 1.7 g (5 mmol) of the compound prepared by the method of ExampleI-4-a-6 are initially charged in 20 ml of ethyl acetate p.a. At 20° C.,0.5 g (5 mmol) of triethylamine are added, and at 0° C. 0.39 g (5 mmol)of ClCOCH₃ in 5 ml of ethyl acetate are added dropwise. The reaction iscarried out with the exclusion of moisture. The mixture is stirred at20° C. for 20 hours. The precipitate is separated off and washed withethyl acetate. The organic phase is washed with twice 25 ml ofhalf-concentrated NaCl solution, dried over sodium sulphate andevaporated.

[0775] Yield: 1 g (53% of theory), mp.: 170 to 172° C.

[0776] The compounds of the formula (I-4-b) given below are obtainedanalogously or in accordance with the general preparation instructions.TABLE 65-a (I-4-b)

Ex No. V W X Y Z A D G m.p. ° C. I-4-b-2 H CH₃ CH₃ CH₃ CH₃ CH₃ 2-PyridylCOCH₃ 170-172 I-4-b-3 H CH₃ CH₃ CH₃ CH₃ CH₃ 2-PyridylCO-(6-Cl-3-Pyridyl) 96-98 I-4-b-4 H CH₃ CH₃ CH₃ CH₃ CH₃ 2-PyridylCO-4-Cl—C₆H₄ 100-102

Example (I-4-c-1)

[0777]

[0778] 1.7 (5 mmol) of the compound prepared by the method of ExampleI-4-a-6 are initially charged in 20 ml of ethyl acetate p.a. At 20° C.,0.5 g (5 mmol) of triethylamine are added, and at 0° C. 0.47 g (5 mmol)of ClCO₂CH₃ in 5 ml of ethyl acetate are added dropwise. The reaction iscarried out with the exclusion of moisture. The mixture is stirred at20° C. for 20 hours. For work-up, the precipitate is separated off andwashed with ethyl acetate. The organic phase is washed with twice 25 mlof half-concentrated NaCl solution, dried over sodium sulphate andevaporated

[0779] Yield 16 g (81% of theory), mp.: 136 to 139° C.

Example (VI-1)

[0780]

[0781] At room temperature, 31 ml of thionyl chloride are added dropwiseto 15 g (63.5 mmol) of the compound prepared by the method of Example(XXXIII-1) in 20 ml of toluene, and the solution is stirred initiallyfor 1 hour at room temperature and then at about 95° C. overnight. Aftercooling, HCl and SO₂ are blown off at about 45° C. by passing argonthrough the solution, and remaining volatile compounds are subsequentlyremoved using high vacuum.

[0782] Yield: 7.4 g (52% of theory), bp.: 110-111° C./0.08 mbar.

Example (VI-2)

[0783] Analogously to Example (VI-1) or according to the generalpreparation procedures, the compound

[0784] is obtained.

[0785]¹H-NMR (400 MHz, CDCl₃): δ=2.13 (s, 3H, Ar—CH₃), 2.22 (s, 3H,Ar—CH₃), 2.28 (s, 6H, 2×Ar—CH₃); 6.94 (s, 1H, Ar—H).

Example (XXXIII-1)

[0786]

[0787] At room temperature, 40 g (0.155 mol) of the compound prepared bythe method of Example (XXXIV-1) are added to 28.2 g of potassiumhydroxide in 37.8 g of water and 75.6 ml of methanol, and the mixture isheated under reflux for 10 hours

[0788] After cooling, the mixture is concentrated under reducedpressure, the residue is dissolved in about 100 ml of ice water and,while cooling, acidified with half-concentrated hydrochloric acid. Thephases are separated and extracted with toluene. The solid whichseparates off is filtered off with suction, stirred with a littletoluene and filtered off under suction once more.

[0789] Yield. 35.20 g (70.3% of theory). mp.: 193-198° C.

Example (XXXIII-2)

[0790] Analogously to Example (XXXIII-1) or according to the generalpreparation instructions, the compound

[0791] of mp.: 181° C. (decomposition) is obtained.

Example (XXXIV-1)

[0792]

[0793] At room temperature, 350 g (3.5 mol) of dimethyl carbonate andthen, slowly, at 85-90° C., 42.0 g (0.203 mol) of methyl2,3,5,6-tetramethylphenylacetate are added dropwise to 7.9 g (0.264 mol)of 80% strength sodium hydride, and the mixture is stirred overnight.After cooling, a little methanol is added to the mixture which is thenpoured into about 1 l of ice water and acidified with half-concentratedhydrochloric acid. The organic phase is separated off, the aqueous phaseis extracted with toluene, and the combined organic phases are dried andconcentrated. The residue is subsequently distilled using high vacuum.

[0794] Yield: 41.9 g (82% of theory). mp.: 125-129° C.

[0795] Analogously to Example (XXXIV-1) and according to the generalpreparation instructions, the compound

[0796] of mp: 132-134° C. is obtained.

Example (XXIII-1)

[0797]

[0798] At room temperature, 171.9 g of the compound prepared by themethod of Example XXVI-1 are added dropwise to a mixture of 85.8 g(1.532 mol) of KOH in 110.2 ml of water and 224 ml of methanol, and themixture is heated under reflux for 5 h. After cooling, the mixture isdiluted with 300 ml of water and washed with methyl tert-butyl ether.The aqueous phase is acidified with half-concentrated hydrochloric acid,filtered off with suction and dried, and the residue is recrystallizedfrom toluene.

[0799] Yield: 111.4 g (Δ69% of theory) mp.: 128-130° C.

[0800] The compounds of the formula (XXIII) given below were obtainedanalogously to Example (XXIII-1) and according to the generalpreparation instructions: TABLE 66 (XXIII)

Ex. No. V W X Y Z mp. ° C. XXIII-2 H CH₃ CH₃ H Br 112 XXIII-3 H Cl Cl HBr 157 XXIII-4 H Br Br —(CH₂)₃— 175 XXIII-5 H Br Br Br CH₃ 217-220XXIII-6 H Cl Cl Cl CH₃ 176-179

Example (XXIV-1)

[0801]

[0802] At room temperature, 992 ml of 30% strength sodium methoxidesolution in methanol are added dropwise to a solution of 353.7 g (1.3mol) of the compound prepared by the method of Example XXV-1 in 560 mlof methanol, and the mixture is boiled under reflux for 5 hours. Aftercooling to room temperature, 148 ml of conc. sulphuric acid are addeddropwise, and the mixture is heated under reflux for 1 hour, cooled,concentrated, admixed with water, extracted with methylene chloride,dried and concentrated. 179.1 g of an oil of the desired product XXIV-1(about 51% according to GC), the acid XXIII-1 and1,3-dichloro-2,6-dimethylbenzene are obtained. This mixture was used forthe reaction of Example XXIII-1.

[0803] The compounds of the formula (XXIV) given below were obtainedanalogously to Example (XXIV-1) and according to the general preparationinstructions: TABLE 67 (XXIV)

Ex. No. V W X Y Z R⁸ bP_(mbar ° C.) XXIV-2 H CH₃ CH₃ H Br CH₃ * XXIV-3 HCl Cl H Br CH₃ 85-92 0.1 mbar XXIV-4 H Br Br —(CH₂)₃— CH₃ * XXIV-5 H BrBr Br CH₃ CH₃ 143 0.08 mbar XXIV-6 H Cl Cl Cl CH₃ CH₃ 138 0.4 mbar

Example (XXV-1)

[0804]

[0805] 2205 g (22.8 mol) of 1,1-dichloroethylene (vinylidene chloride)are added dropwise to a well-cooled mixture of 229.7 g (2.27 mol) oftert-butyl nitrite and 255 g (1.776 mol) of anhydrous copper-(II)chloride in 990 ml of anhydrous acetonitrile, the mixture being kept atroom temperature. Then, at a temperature of below 30° C., a mixture of232 g (1.49 mol) of 3-chloro-2,6-dimethylaniline in 1500 ml of anhydrousacetonitrile is added dropwise. At room temperature, the mixture isstirred until the formation of gas has ceased, and the mixture is thencarefully poured into 6 liters of 20% strength hydrochloric acid andextracted with methylene chloride. The organic phases are combined,washed once more with 20% strength hydrochloric acid, dried andconcentrated. The remaining oil is used without any further work-up forthe reaction of Example (XXIV-1).

[0806] The compounds of the formula (XXV) given below were obtainedanalogously to Example (XXV-1) and according to the general preparationinstructions: TABLE 68 (XXV)

Ex. No. V W X Y Z XXV-2 H CH₃ CH₃ H Br XXV-3 H Cl Cl H Br XXV-4 H Br Br—(CH₂)₃— XXV-5 H Br Br Br CH₃ XXV-6 H Cl Cl Cl CH₃

[0807] The compounds listed in Table 68 were employed as crude productsin the saponification reaction leading to compounds of the formula(XXIV), and were, for that reason, not further characterized.

USE EXAMPLES Example 1

[0808] Phaedon larvae test

[0809] Solvent: 7 parts by weight of dimethylformamide

[0810] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0811] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0812] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of the active compound of the desired concentrationand are infested with mustard beetle larvae (Phaedon cochleariae) whilethe leaves are still moist.

[0813] After the specified period of time, the destruction in % isdetermined. 100% means that all the beetle larvae have been killed; 0%means that none of the beetle larvae have been killed.

[0814] In this test, for example the compounds of Preparation Examples(I-1-a-2), (I-1-a-3), (I-1-b-1), (I-1-b-2) and (I-1-c-1) at an exemplaryactive compound concentration of 1000 ppm caused a destruction of 100%after 7 days.

Example 2

[0815] Tetranychus test (OP resistant/spray treatment)

[0816] Solvent: 3 parts by weight of dimethylformamide

[0817] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0818] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentrations.

[0819] Bean plants (Phaseolus vulgaris) heavily infected by all stagesof the spider mite (Tetranychus urticae) are sprayed with a preparationof the active compound of the desired concentration.

[0820] After the specified period of time, the destruction in % isdetermined. 100% means that all spider mites have been killed; 0% meansthat none of the spider mites have been killed.

[0821] In this test, an activity of 100% was shown, after 7 days, forexample by the compound of Preparation Example (I-1-a-2) at an exemplaryactive compound concentration of 1000 ppm.

Example 3

[0822] Plutella test

[0823] Solvent: 7 parts by weight of dimethylformamide

[0824] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0825] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0826] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare infested with caterpillars of the diamond-back moth (Plutellamaculipennis) while the leaves are still moist.

[0827] After the specified period of time, the destruction in % isdetermined. 100% means that all the caterpillars have been killed; 0%means that none of the caterpillars have been killed.

[0828] In this test, for example the compounds of Preparation Examples(I-1-a-3), (I-1-b-1), (I-1-b-2), (I-1-b-6) and (I-1-c-1) at an exemplaryactive compound concentration of 0.1% caused a destruction of 100% after7 days.

Example 4

[0829] Spodoptera test

[0830] Solvent: 7 parts by weight of dimethylformamide

[0831] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0832] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0833] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of the active compound of the desired concentrationand are infested with caterpillars of the owlet moth (Spodopterafrugiperda), as long as the leaves are still moist.

[0834] After the specified period of time, the destruction in % isdetermined. 100% means that all the caterpillars have been killed; 0%means that none of the caterpillars have been killed.

[0835] In this test, for example the compounds of Preparation Examples(I-1-a-2), (I-1-a-3) and (I-1-b-4) at an exemplary active compoundconcentration of 0.1% caused a destruction of at least 80% after 7 days.

Example 5

[0836] Nephotettix test

[0837] Solvent 7 parts by weight of dimethylformamide

[0838] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0839] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0840] Rice seedlings (Oryzae sativa) are treated by being dipped intothe preparation of the active compound of the desired concentration andare infested with larvae of the green rice leafhopper (Nephotettixcincticeps) while the seedlings are still moist.

[0841] After the specified period of time, the destruction in % isdetermined. 100% means that all the leafhoppers have been killed; 0%means that none of the leafhoppers have been killed.

[0842] In this test, for example, the compounds of Preparation Examples(I-1-a-1), (I-1-a-2), (I-1-a-3), (I-1-b-1), (I-1-b-2), (I-1-b-3),(I-1-b-4), (I-1-b-5), (I-1-b-6) and (I-1-c-2) at an exemplary activecompound concentration of 0.1% caused a destruction of 100% after 6days.

Example 6

[0843] Myzus test

[0844] Solvent: 7 parts by weight of dimethylformamide

[0845] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0846] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0847] Cabbage leaves (Brassica oleracea) which have been heavilyinfested with the peach aphid (Myzus persicae) are treated by beingdipped into the preparation of the active compound of the desiredconcentration.

[0848] After the specified period of time, the destruction in % isdetermined. 100% means that all the aphids have been killed; 0% meansthat none of the aphids have been killed.

[0849] In this test, for example, the compounds according to PreparationExamples (I-1-a-1), (I-1-a-2), (I-1-a-3), (I-1-b-2), (I-1-b-3) and(I-2-a-1) at an exemplary active compound concentration of 0.1% caused adestruction of at least 80% after 6 days

Example 7

[0850] Tetranychus test (OP resistant/dip treatment)

[0851] Solvent: 3 parts by weight of dimethylformamide

[0852] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0853] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0854] Bean plants (Phaseolus vulgaris) heavily infected by all stagesof the spider mite (Tetranychus urticae) are dipped into a preparationof the active compound of the desired concentration.

[0855] After the specified period of time, the destruction in % isdetermined. 100% means that all spider mites have been killed; 0% meansthat none of the spider mites have been killed.

[0856] In this test, a destruction of 100% was caused, after 5 days, forexample by the compounds of Preparation Examples (I-1-a-1), (I-1-a-2),(I-1-a-3), (I-1-b-2) and (I-2-b-1) at an exemplary active compoundconcentration of 0.1%.

1. Compounds of the formula (I)

in which V represents hydrogen, halogen, alkyl or alkoxy, W representscyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl,halogenoalkoxy, respectively optionally substituted phenyl, phenoxy,phenylthio, phenylalkoxy or phenylalkylthio, X represents hydrogen,halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy,cyano, nitro or respectively optionally substituted phenyl, phenoxy,phenylthio, phenylalkyloxy or phenylalkylthio, Y represents hydrogen,halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro, Zrepresents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy,hydroxyl, cyano, nitro or respectively optionally substituted phenoxy,phenylthio, 5- to 6-membered hetaryloxy, 5- to 6-membered hetarylthio,phenylalkyloxy or phenylalkylthio, Y and Z represent together with thecarbon atoms that they are attached to an optionally substituted cyclewhich is optionally interrupted by one or more heteroatoms, V, X and Whaving one of the above-mentioned meanings, or W and Z representtogether with the carbon atoms that they are attached to an optionallysubstituted cycle which is optionally interrupted by one or moreheteroatoms, V, X and Y having one of the above-mentioned meanings, Hetrepresents one of the groups

 in which A represents hydrogen, respectively optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl oralkylthioalkyl, respectively saturated or unsaturated and optionallysubstituted cycloalkyl or heterocyclyl or respectively optionallyhalogen-, alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- ornitro- substituted aryl, arylalkyl or hetaryl, B represents hydrogen,alkyl or alkoxyalkyl, or A and B represent together with the carbon atomthat they are attached to a saturated or unsaturated optionallysubstituted carbocycle or heterocycle, D represents hydrogen or anoptionally substituted radical from the group consisting of alkyl,alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl,saturated or unsaturated cycloalkyl, saturated or unsaturatedheterocyclyl, arylalkyl, aryl, hetarylalkyl or hetaryl, or A and Drepresent together with the atoms that they are attached to arespectively optionally substituted carbocycle or heterocycle, Grepresents hydrogen (a) or one of the groups

 in which, E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur, M represents oxygen or sulphur, R¹represents respectively optionally halogen-substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or respectivelyoptionally halogen-, alkyl- or alkoxy-substituted cycloalkyl orheterocyclyl or respectively optionally substituted phenyl, phenylalkyl,hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² represents respectivelyoptionally halogen-substituted alkyl, alkenyl, alkoxyalkyl orpolyalkoxyalkyl or respectively optionally substituted cycloalkyl,phenyl or benzyl, R³, R⁴ and R⁵ each represent independently of oneanother respectively optionally halogen-substituted alkyl, alkoxy,alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio orrespectively optionally substituted phenyl, benzyl, phenoxy orphenylthio, R⁶ and R⁷ each represent independently of one anotherhydrogen, respectively optionally halogen-substituted alkyl, cycloalkyl,alkenyl, alkoxy or alkoxyalkyl or respectively optionally substitutedphenyl or benzyl, or represent together with the N-atom that they areattached to an optionally oxygen- or sulphur-containing and optionallysubstituted cycle, excluding the following compounds


2. Process for preparing compounds of the formula (I) according to claim1 , characterized in that (A) compounds of the formula (I-1-a)

 in which A, B, V, W, X, Y and Z are each as defined above, are obtainedby the intramolecular condensation of compounds of the formula (II)

 in which, A, B, V, W, X, Y and Z are each as defined above and R⁸represents alkyl (preferably C₁-C₆-alkyl) in the presence of a diluentand in the presence of a base, (B) compounds of the formula (I-2-a)

 in which A, B, V, W, X, Y and Z are each as defined above are obtainedby the intramolecular condensation of compounds of the formula (III)

 in which A, B, V, W, X, Y, Z and R⁸ are each as defined above in thepresence of a diluent and in the presence of a base, (C) compounds ofthe formula (I-3-a)

 in which A, B, V, W, X, Y and Z are each as defined above are obtainedby the intramolecular cyclization of compounds of formula (IV)

 in which A, B, V, W, X, Y, Z and R⁸ are each as defined above and Trepresents hydrogen, halogen, alkyl (preferably C₁-C₆-alkyl) or alkoxy(preferably C₁-C₈-alkoxy),  if appropriate in the presence of a diluentand in the presence of an acid, (D) compounds of the formula (I-4-a)

 in which A, D, V, W, X, Y and Z are each as defined above are obtainedby reacting compounds of the formula (V)

 in which A and D are each as defined above or their silyl enol ethersof the formula (Va)

 in which A and D are each as defined above and R^(8′) represents alkyl(preferably methyl) with compounds of the formula (VI)

 in which V, A, X, Y and Z are each as defined above and Hal representshalogen (preferably chlorine or bromine), if appropriate in the presenceof a diluent and if appropriate in the presence of an acid acceptor, (E)compounds of the formula (I-5-a)

 in which A, V, W, X, Y and Z are each as defined above are obtained byreacting compounds of the formula (VII)

 in which A is as defined above with compounds of the formula (VI)

 in which Hal, V, W, X, Y and Z are each as defined above, ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid acceptor, and by optionally subsequently reactingthe compounds of the formulae (I-1-a) to (I-5-a) obtained in this manner(Fα) with acid halides of the formula (VIII)

 in which R¹ is as defined above and Hal represents halogen (inparticular chlorine or bromine) or (Fβ) with carboxylic anhydrides ofthe formula (IX) R¹—CO—O—CO—R¹   (IX)  in which R¹ is as defined above,if appropriate in the presence of a diluent and if appropriate in thepresence of an acid-binding agent; or (G) with chloroformic esters orchloroformic thioesters of the formula (X) R²—M—CO—Cl   (X)  in which R²and M are each as defined above, if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent; or(Hα) with chloromonothioformic esters or chlorodithioformic esters ofthe formula (XI)

 in which M and R² are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent or (Hβ) with carbon disulphide and subsequently withcompounds of the formula (XII) R²-Hal   (XII)  in which R² is as definedabove and Hal represents chlorine, bromine or iodine, if appropriate inthe presence of a diluent and if appropriate in the presence of a base,or (I) with sulphonyl chlorides of the formula (XIII) R³—SO₂—Cl   (XII) in which R³ is as defined above, if appropriate in the presence of adiluent and if appropriate in the presence of an acid-binding agent, or(J) with phosphorus compounds of the formula (XIV)

 in which L, R⁴ and R⁵ are each as defined above and Hal representshalogen (in particular chlorine or bromine), if appropriate in thepresence of a diluent and if appropriate in the presence of acid-bindingagent, or (K) with metal compounds or amines of the formulae (XV) or(XVI) Me(OR¹⁰)_(t)   (XV)

 in which Me represents a mono- or divalent metal (preferably an alkalimetal or an alkaline earth metal such as lithium, sodium, potassium,magnesium or calcium), t represents the number 1 or 2 and R¹⁰, R¹¹, R¹²each independently of one another represent hydrogen or alkyl(preferably C₁-C₈-alkyl), if appropriate in the presence of a diluent,or (Lα) with isocyanates or isothiocyanates of the formula (XVII)R⁶—N═C═L   (XVII)  in which R⁶ and L are each as defined above, ifappropriate in the presence of a diluent and if appropriate in thepresence of a catalyst or (Lβ) with carbamoyl chlorides or thiocarbamoylchlorides of the formula (XVIII)

 in which L, R⁶ and R⁷ are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of anacid-binding agent.
 3. Compounds of the formula (I) according to claim 1in which V represents hydrogen, halogen, C₁-C₆-alkyl or C₁-C₆-alkoxy, Wrepresents cyano, nitro, halogen, C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxyor respectively optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenoxy, phenylthio, phenyl-C₁-C₄-alkoxy orphenyl-C₁-C₄-alkylthio, X represents hydrogen, halogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkinyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, cyano, nitro or respectively optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy,phenylthio, phenyl-C₁-C₄-alkoxy or phenyl-C₁-C₄-alkylthio, Y representshydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, cyano or nitro, Z represents halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, hydroxyl,cyano, nitro or respectively optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenoxy, phenylthio, thiazolyloxy, pyridinyloxy,pyrimidyloxy, pyrazolyloxy, phenyl-C₁-C₄-alkyloxy orphenyl-C₁-C₄-alkylthio, or, Y and Z together represent respectivelyoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy- orC₁-C₄-halogenoalkyl-substituted C₃-C₅-alkanediyl or C₃-C₅-alkenediyl inwhich one to three members can be optionally replaced independently ofone another by oxygen, sulphur, nitrogen or a carbonyl group, or W and Ztogether represent respectively optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₅-alkanediyl orC₃-C₅-alkenediyl in which one to three members can be optionallyreplaced independently of one another by oxygen, sulphur, nitrogen or acarbonyl group, Het represents one of the groups

A represents hydrogen, respectively optionally halogen-substitutedC₁-C₁₂-alkyl, C₂-C₈-alkenyl, C₁-C₁₀-alkoxy-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or C₁-C₁₀-alkylthio-C₁-C₆-alkyl,optionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl in which optionally one or two not directly adjacentmethylene groups are replaced by oxygen and/or sulphur or representsrespectively optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- or nitro-substitutedphenyl, naphthyl, phenyl-C₁-C₆-alkyl, naphthyl-C₁-C₆-alkyl or hetarylhaving 5 or 6 ring atoms and one to three heteroatoms from the groupconsisting of oxygen, sulphur and nitrogen, B represents hydrogen,C₁-C₁₂-alkyl or C₁-C₈-alkoxy-C₁-C₆-alkyl or A, B and the carbon atomthat they are attached to represent C₃-C₁₀-cycloalkyl orC₅-C₁₀-cycloalkenyl where in each case one methylene group is optionallyreplaced by oxygen or sulphur and which are optionally substituted byC₁-C₈-alkyl, C₃-C₁₀-cycloalkyl, C₁-C₈-halogenoalkyl, C₁-C₈-alkoxy,C₁-C₈-alkylthio, halogen or phenyl, or A, B and the carbon atom thatthey are attached to represent C₅-C₆-cycloalkyl which is substituted byan alkylenediyl group optionally containing one or two oxygen and/orsulphur atoms or by an alkylenedioxy group or alkylenedithioyl groupforming a further five- to eight-membered ring with the carbon atom thatit is attached to, or A, B and the carbon atom that they are attached torepresent C₃-C₈-karin cycloalkyl or C₅-C₈-cycloalkenyl in which twocarbon atoms are connected by respectively optionally C₁-C₆-alkyl-,C₁-C₆-alkoxy- or halogen-substituted C₃-C₆-alkanediyl, C₃-C₆-alkenediylor C₄-C₆-alkanedienediyl where in each case one methylene group isoptionally replaced by oxygen or sulphur, D represents hydrogen,respectively optionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₃-C₈-alkinyl, C₁-C₁₀-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkylor C₁-C₁₀-alkylthio-C₂-C₈-alkyl, optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-alkoxy- or C₁-C₄-halogenoalkyl-substituted C₃-C₈-cycloalkyl inwhich optionally one or two not directly adjacent methylene groups arereplaced by oxygen and/or sulphur, or represents respectively optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkoxy-, cyano- or nitro-substituted phenyl, hetarylhaving 5 to 6 ring atoms and one or two heteroatoms from the groupconsisting of oxygen, sulphur and nitrogen, phenyl-C₁-C₆-alkyl orhetaryl-C₁-C₆-alkyl having 5 to 6 ring atoms and one or two heteroatomsfrom the group consisting of oxygen, sulphur and nitrogen, or A and Dtogether represent a C₃-C₆-alkanediyl, C₃-C₆-alkenediyl orC₄-C₆-alkadienediyl group in which in each case one methylene group isoptionally replaced by oxygen or sulphur and which are respectivelyoptionally substituted by halogen or by respectively optionallyhalogen-substituted C₁-C₁₀-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,C₃-C₇-cycloalkyl, phenyl or benzyloxy or by a further C₃-C₆-alkanediyl,C₃-C₆-alkenediyl or C₄-C₆-alkadienediyl group forming a fused-on ringwhere in each case one methylene group is optionally replaced by oxygenor sulphur and which are optionally substituted by C₁-C₆-alkyl, or A andD together represent a C₃-C₆-alkanediyl or C₃-C₆-alkenediyl group, eachof which optionally contains one of the following groups

G represents hydrogen (a) or one of the groups

in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents respectively optionally halogen-substituted C₁-C₂₀-alkyl,C₂-C₂₀-alkenyl, C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl orpoly-C₁-C₈-alkoxy-C₁-C₈-alkyl or respectively halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which one or two notdirectly adjacent methylene groups are optionally replaced by oxygenand/or sulphur, optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl, optionallyhalogen-, nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl, optionally halogen- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryl having one or two heteroatoms from the groupconsisting of oxygen, sulphur and nitrogen, optionally halogen- orC₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl or optionally halogen-,amino- or C₁-C₆-alkyl-substituted 5- or 6-memberedhetaryloxy-C₁-C₆-alkyl having one or two heteroatoms from the groupconsisting of oxygen, sulphur and nitrogen, R² represents respectivelyoptionally halogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl or poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, optionallyhalogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl orrespectively optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl or C₁-C₆-halogenoalkoxy-substitutedphenyl or benzyl, R³ represents optionally halogen-substitutedC₁-C₈-alkyl or respectively optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano- ornitro-substituted phenyl or benzyl, R⁴ and R⁵ each representindependently of one another respectively optionally halogen-substitutedC₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino,C₁-C₈-alkylthio or C₃-C₈-alkenylthio, respectively optionally halogen-,nitro-, cyano-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-,C₁-C₄-halogenoalkylthio-, C₁-C₄-alkyl- orC₁-C₄-halogenoalkyl-substituted phenyl, phenoxy or phenylthio, R⁶ and R⁷represent independently of one another hydrogen, respectively optionallyhalogen-substituted C₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy,C₃-C₈-alkenyl or C₁-C₈-alkoxy-C₂-C₈-alkyl, respectively optionallyhalogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- or C₁-C₈-alkoxy-substitutedphenyl or benzyl or together represent an optionallyC₁-C₆-alkyl-substituted C₃-C₆-alkylene radical in which one methylenegroup is optionally replaced by oxygen or sulphur, R¹³ representshydrogen or respectively optionally halogen-substituted C₁-C₈-alkyl orC₁-C₈-alkoxy, optionally halogen-, C₁-C₄-alkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which one methylene groupis optionally replaced by oxygen or sulphur, or respectively optionallyhalogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₄-alkyl or phenyl-C₁-C₄-alkoxy, R¹⁴ represents hydrogen orC₁-C₈-alkyl or R¹³ and R¹⁴ together represent C₄-C₆-alkanediyl, R¹⁵ andR¹⁶ are identical or different and represent C₁-C₆-alkyl or R¹⁵ and R¹⁶together represent a C₂-C₄-alkanediyl radical which is optionallysubstituted by C₁-C₆-alkyl or by optionally halogen-, C₁-C₄-alkyl-,C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-, nitro- orcyano-substituted phenyl, R¹⁷ and R¹⁸ each represent independently ofone another hydrogen, optionally halogen-substituted C₁-C₈-alkyl oroptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl or R¹⁷ and R¹⁸represent together with the carbon atom that they are attached tooptionally C₁-C₄-alkyl-substituted C₅-C₇-cycloalkyl in which onemethylene group is optionally replaced by oxygen or sulphur and R¹⁹ andR²⁰ each represent independently of one another C₁-C₁₀-alkyl,C₂-C₁₀-alkenyl, C₁-C₁₀-alkoxy, C₁-C₁₀-alkylamino, C₃-C₁₀-alkenylamino,di-(C₁-C₁₀-alkyl)amino or di-(C₃-C₁₀-alkenyl)amino), excluding thefollowing compounds


4. Compounds of the formula (I) according to claim 1 in which Vrepresents hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl orC₁-C₄-alkoxy, W represents cyano, nitro, fluorine, chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy orrespectively optionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-,C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, nitro- orcyano-substituted phenyl, phenoxy, benzyl or benzyloxy, X representshydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, cyano, nitro or respectivelyoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, nitro- or cyano-substitutedphenyl, phenoxy, benzyl or benzyloxy, Y represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, cyano or nitro, Z represents fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-,C₁-C₂-halogenoalkyl-, C₁-C₂-halogenoalkoxy-, nitro- or cyano-substitutedphenoxy or benzyloxy, or Y and Z together represent respectivelyoptionally fluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-or C₁-C₂-halogenoalkyl-substituted C₃-C₄-alkanediyl or C₃-C₄-alkenediylin which optionally one or two not directly adjacent members arereplaced independently of one another by oxygen, sulphur or nitrogen, orW and Z together represent respectively optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- or C₁-C₂-halogenoalkyl-substitutedC₃-C₄-alkanediyl or C₃-C₄-alkenyldiyl in which optionally one or two notdirectly adjacent members are replaced independently of one another byoxygen, sulphur or nitrogen, Het represents one of the groups

A represents hydrogen, respectively optionally fluorine- orchlorine-substituted C₁-C₁₀-alkyl, C₂-C₆-alkenyl,C₁-C₈-alkoxy-C₁-C₆-alkyl, poly-C₁-C₆-alkoxy-C₁-C₆-alkyl orC₁-C₈-alkylthio-C₁-C₆-alkyl or optionally fluorine-, chlorine-,C₁-C₄-alkyl or C₁-C₄-alkoxy-substituted C₃-C₇-cycloalkyl in which one ortwo not directly adjacent methylene groups are optionally replaced byoxygen and/or sulphur, or respectively optionally fluorine-, chlorine-,bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl, furanyl,pyridyl, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienylor phenyl-C₁-C₄-alkyl, B represents hydrogen, C₁-C₁₀-alkyl orC₁-C₆-alkoxy-C₁-C₄-alkyl or A, B and the carbon atom that they areattached to represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl in whichrespectively optionally one methylene group is replaced by oxygen orsulphur and which are optionally substituted by C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₁-C₃-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,fluorine, chlorine or phenyl, or A, B and the carbon atom that they areattached to represent C₅-C₆-cycloalkyl which is substituted by analkylenediyl group optionally containing one or two oxygen or sulphuratoms, or by an alkylenedioxy or alkylenedithiol group forming a furtherfive- to seven-membered ring with the carbon atom that it is attached toor A, B and the carbon atom that they are attached to representC₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in which two carbon atoms areconnected by optionally C₁-C₄-alkyl-, C₁-C₄-alkoxy-, fluorine-,chlorine- or bromine-substituted C₃-C₅-alkanediyl, C₃-C₅-alkenediyl orbutadienediyl in which respectively optionally one methylene group isreplaced by oxygen or sulphur, D represents hydrogen, respectivelyoptionally fluorine- or chlorine-substituted C₁-C₁₀-alkyl,C₃-C₆-alkenyl, C₃-C₆-alkinyl, C₁-C₈-alkoxy-C₂-C₆-alkyl,poly-C₁-C₆-alkoxy-C₂-C₆-alkyl or C₁-C₈-alkylthio-C₂-C₆-alkyl, optionallyfluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which one or two notdirectly adjacent methylene groups are optionally replaced by oxygenand/or sulphur, or represents respectively optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl, furanyl,imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl,triazolyl or phenyl-C ₁-C₄-alkyl or A and D represent a C₃-C₅-alkanediylor C₃-C₅-alkenediyl group in which respectively optionally one carbonatom is replaced by oxygen or sulphur and which are optionallysubstituted by fluorine, chlorine or respectively optionally fluorine-or chlorine-substituted C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₃-C₆-cycloalkyl, phenyl or benzyloxy or which respectively optionallycontain one of the following groups:

G represents hydrogen (a) or one of the groups

 in which E represents a metal ton equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents respectively optionally fluorine- or chlorine-substitutedC₁-C₁₆-alkyl, C₂-C₁₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl or poly-C₁-C₆-alkoxy-C₁-C₆-alkyl oroptionally fluorine-, chlorine-, C₁-C₅-alkyl- orC₁-C₅-alkoxy-substituted C₃-C₇-cycloalkyl in which one or two notdirectly adjacent methylene groups are optionally replaced by oxygenand/or sulphur, optionally fluorine-, chlorine-, bromine-, cyano-,nitro-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-,C₁-C₃-halogenoalkoxy-, C₁-C₄-alkylthio- orC₁-C₄-alkylsulphonyl-substituted phenyl, optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₃-halogenoalkyl-or C₁-C₃-halogenoalkoxy-substituted phenyl-C₁-C₄-alkyl, optionallyfluorine-, chlorine-, bromine- or C₁-C₄-alkyl-substituted pyrazolyl,thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, optionally fluorine-,chlorine-, bromine- or C₁-C₄-alkyl-substituted phenoxy-C₁-C₅-alkyl orrespectively optionally fluorine-, chlorine-, bromine-, amino- orC₁-C₄-alkyl-substituted pyridyloxy-C₁-C₅-alkyl, pyrimidyloxy-C₁-C₅-alkylor thiazolyloxy-C₁-C₅-alkyl, R² represents respectively optionallyfluorine- or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₆-alkoxy-C₂-C₆-alkyl or poly-C₁-C₆-alkoxy-C₂-C₆-alkyl, optionallyfluorine-, chlorine-, C₁-C₄-alkyl- or C₁-C₄-alkoxy-substitutedC₃-C₇-cycloalkyl or respectively optionally fluorine-, chlorine-,bromine-, cyano-, nitro-, C₁-C₄-alkyl-, C₁-C₃-alkoxy-,C₁-C₃-halogenoalkyl- or C₁-C₃-halogenoalkoxy-substituted phenyl orbenzyl, R³ represents optionally fluorine- or chlorine-substitutedC₁-C₆-alkyl or respectively optionally fluorine-, chlorine-, bromine-,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkoxy-, C₁-C₂-halogenoalkyl-, cyano- or nitro-substituted phenyl or benzyl, R⁴ and R⁵ eachrepresent independently of one another respectively optionally fluorine-or chlorine-substituted C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio or C₃-C₄-alkenylthio orrespectively optionally fluorine-, chlorine-, bromine-, nitro-, cyano-,C₁-C₃-alkoxy-, C₁-C₃-halogenoalkoxy-, C₁-C₃-alkylthio-,C₁-C₃-halogenoalkylthio, C₁-C₃-alkyl- or C₁-C₃-halogenoalkyl-substitutedphenyl, phenoxy or phenylthio, R⁶ and R⁷ each represent independently ofone another hydrogen, respectively optionally fluorine- orchlorine-substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,C₃-C₆-alkenyl or C₁-C₆-alkoxy-C₂-C₆-alkyl, respectively optionallyfluorine-, chlorine-, bromine-, C₁-C₅-halogenoalkyl-, C₁-C₅-alkyl- orC₁-C₅-alkoxy-substituted phenyl or benzyl, or represent together anoptionally C₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which onemethylene group is optionally replaced by oxygen or sulphur, R¹³represents hydrogen or respectively optionally fluorine- orchlorine-substituted C₁-C₆-alkyl or C₁-C₆-alkoxy, optionally fluorine-,C₁-C₂-alkyl- or C₁-C₂-alkoxy-substituted C₃-C₇-cycloalkyl in which onemethylene group is optionally replaced by oxygen or sulphur, orrepresents respectively optionally fluorine-, chlorine-, bromine-,C₁-C₅-alkyl-, C₁-C₅-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl,phenyl-C₁-C₃-alkyl or phenyl-C₁-C₂-alkyloxy, R¹⁴ represents hydrogen orC₁-C₆-alkyl or R¹³ and R¹⁴ together represent C₄-C₆-alkanediyl, R¹⁵ andR¹⁶ are identical or different and represent C₁-C₄-alkyl or R¹⁵ and R¹⁶together represent a C₂-C₃-alkanediyl radical which is optionallysubstituted by C₁-C₄-alkyl or optionally fluorine-, chlorine-, bromine-,C₁-C₂-alkyl-, C₁-C₂-halogenoalkyl-, C₁-C₂-alkoxy-,C₁-C₂-halogenoalkoxy-, nitro- or cyano-substituted phenyl, excluding thefollowing compounds


5. Compounds of the formula (I) according to claim 1 in which Vrepresents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl,isopropyl, tert-butyl, methoxy, ethoxy, propoxy or isopropoxy, Wrepresents cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl,propyl, butyl, isopropyl, isobutyl, tert-butyl, methoxy, ethoxy,propoxy, isopropoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy,phenyl or benzyloxy, X represents hydrogen, fluorine, chlorine, bromine,methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert-butyl, methoxy,ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy,difluoromethoxy, cyano, nitro, phenyl or benzyloxy, Y representshydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl,butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy,trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, Zrepresents fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl,isobutyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy,trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, or Yand Z together represent optionally fluorine-, chlorine-, methyl-,ethyl-, propyl-, isopropyl-, methoxy-, ethoxy-, propoxy-, isopropoxy- ortrifluoromethyl-substituted C₃-C₄-alkanediyl in which two not directlyadjacent members are optionally replaced by oxygen, or W and Z togetherrepresent optionally fluorine-, chlorine-, methyl-, ethyl-, propyl-,isopropyl-, methoxy-, ethoxy-, propoxy-, isopropoxy- ortrifluoromethyl-substituted C₃-C₄-alkanediyl in which two not directlyadjacent members are optionally replaced by oxygen, Het represents oneof the groups

A represents hydrogen, respectively optionally fluorine- orchlorine-substituted C₁-C₈-alkyl, C₂-C₄-alkenyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl orC₁-C₆-alkylthio-C₁-C₄-alkyl or optionally fluorine-, chlorine-, methyl-or methoxy-substituted C₃-C₆-cycloalkyl in which one or two not directlyadjacent methylene groups are optionally replaced by oxygen and orsulphur, or represents respectively optionally fluorine-, chlorine-,bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-, ethoxy-,trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl,pyridyl or benzyl, B represents hydrogen, C₁-C₈-alkyl orC₁-C₄-alkoxy-C₁-C₂-alkyl or A, B and the carbon atom that they areattached to represent C₃-C₈-cycloalkyl or C₅-C₈-cycloalkenyl where ineach case one methylene group is optionally replaced by oxygen orsulphur and which are optionally substituted by methyl, ethyl, n-propyl,isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl,trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy,isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, fluorine,chlorine or phenyl or A, B and the carbon atom that they are attached torepresent C₅-C₆-cycloalkyl which is substituted by an alkylenediyl groupoptionally containing an oxygen or sulphur atom, or by an alkylenedioxygroup forming a further five- or six-membered ring with the carbon atomthat it is attached to or A, B and the carbon atom that they areattached to represent C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl in whichtwo carbon atoms are connected by C₃-C₄-alkanediyl, C₃-C₄-alkenediyl orbutadienediyl, D represents hydrogen, respectively optionally fluorine-or chlorine-substituted C₁-C₈-alkyl, C₃-C₄-alkenyl, C₃-C₄-alkinyl,C₁-C₆-alkoxy-C ₂-C₄-alkyl, poly-C₁-C₄-alkoxy-C₂-C₄-alkyl,C₁-C₄-alkylthio-C₂-C₄-alkyl or C₃-C₆-cycloalkyl in which one or two notdirectly adjacent methylene groups are optionally replaced by oxygenand/or sulphur, or represents respectively optionally fluorine-,chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-,ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl, furanyl, pyridyl, thienyl or benzyl, or A andD together represent a C₃-C₅-alkanediyl or C₃-C₅-alkenediyl group wherein each case one methylene group is optionally replaced by oxygen orsulphur and which are optionally substituted by fluorine, chlorine orrespectively optionally fluorine- or chlorine-substituted C₁-C₆-alkyl orC₁-C₄-alkoxy, G represents hydrogen (a) or one of the groups

 in which E represents a metal ion equivalent or an ammonium ion, Lrepresents oxygen or sulphur and M represents oxygen or sulphur, R¹represents respectively optionally fluorine- or chlorine-substitutedC₁-C₁₄-alkyl, C₂-C₁₄-alkenyl, C₁-C₄-alkoxy-C₁-C₆-alkyl,C₁-C₄-alkylthio-C₁-C₆-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or optionallyfluorine-, chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-,i-butyl-, tert-butyl-, methoxy-, ethoxy-, n-propoxy- orisopropoxy-substituted C₃-C₆-cycloalkyl in which one or two not directlyadjacent methylene groups are optionally replaced by oxygen and/orsulphur, optionally fluorine-, chlorine-, bromine-, cyano-, nitro-,methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-,trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-,methylsulphonyl- or ethylsulphonyl-substituted phenyl, optionallyfluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-,methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substitutedbenzyl, respectively optionally fluorine-, chlorine-, bromine-, methyl-or ethyl-substituted furanyl, thienyl or pyridyl, optionally fluorine-,chlorine-, methyl- or ethyl-substituted phenoxy-C₁-C₄-alkyl orrespectively optionally fluorine-, chlorine-, amino-, methyl- orethyl-substituted pyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl orthiazolyloxy-C₁-C₄-alkyl, R² represents respectively optionallyfluorine- or chlorine-substituted C₁-C₁₄-alkyl, C₂-C₁₄-alkenyl,C₁-C₄-alkoxy-C₂-C₆-alkyl or poly-C₁-C₄-alkoxy-C₂-C₆-alkyl, optionallyfluorine-, chlorine-, methyl-, ethyl-, n-propyl-, isopropyl- ormethoxy-substituted C₃-C₆-cycloalkyl, or respectively optionallyfluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-,i-propyl-, methoxy-, ethoxy-, trifluoromethyl- ortrifluoromethoxy-substituted phenyl or benzyl, R³ represents optionallyfluorine- or chlorine-substituted methyl, ethyl, propyl, isopropyl,butyl, tert-butyl, or respectively optionally fluorine-, chlorine-,bromine-, methyl-, ethyl-, isopropyl-, tert-butyl-, methoxy-, ethoxy-,isopropoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- ornitro-substituted phenyl or benzyl, R⁴ and R⁵ each representindependently of one another respectively optionally fluorine- orchlorine-substituted C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,di-(C₁-C₄-alkyl)amino or C₁-C₄-alkylthio or respectively optionallyfluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-,trifluoromethyl- or trifluoromethoxy-substituted phenyl, phenoxy orphenylthio, R⁶ and R⁷ each represent independently of one anotherhydrogen, respectively optionally fluorine- or chlorine-substitutedC₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl orC₁-C₄-alkoxy-C₂-C₄-alkyl, respectively optionally fluorine-, chlorine-,bromine-, methyl-, methoxy- or trifluoromethyl-substituted phenyl orbenzyl or together represent an optionally methyl- or ethyl-substitutedC₅-C₆-alkylene radical in which one methylene group is optionallyreplaced by oxygen or sulphur, the following compounds

 being excluded.
 6. Compounds of the formula (II)

in which A, B, V, W, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 7. Compounds of the formula (XXI)

in which A, B, V, W, X, Y and Z are each as defined in claim 1 . 8.Compounds of the formula (XXIX)

in which A, B, V, W, X, Y and Z are each as defined in claim 1 . 9.Compounds of the formula (III)

in which A, B, V, W, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 10. Compounds of the formula (IV)

in which A, B, V, W, X, Y and Z are each as defined in claim 1 , R⁸represents alkyl and T represents hydrogen, halogen, alkyl or alkoxy.11. Compounds of the formula (VI)

in which V, W, X, Y and Z are each as defined in claim 1 and Halrepresents chlorine or bromine.
 12. Compounds of the formula (XXIII)

in which V, W, X, Y and Z are each as defined in claim 1 .
 13. Compoundsof the formula (XXIV)

in which V, W, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 14. Compounds of the formula (XXV)

in which V, W, X, Y and Z are each as defined in claim 1 .
 15. Compoundsof the formula (XXXIII)

in which V, W, X, Y and Z are each as defined in claim 1 .
 16. Compoundsof the formula (XXXIV)

in which V, W, X, Y and Z are each as defined in claim 1 and R⁸represents alkyl.
 17. Pesticides or herbicides, characterized in thatthey comprise a compound of the formula (I) according to claim 1 . 18.Use of compounds of the formula (I) according to claim 1 for controllingpests and weeds.
 19. Method for controlling pests and weeds,characterized in that compounds of the formula (I) according to claim 1are allowed to act on pests and weeds and/or their habitat.
 20. Processfor preparing pesticides and herbicides, characterized in that compoundsof the formula (I) according to claim 1 are mixed with extenders and/orsurface-active agents.